U.S. patent number 10,364,243 [Application Number 15/119,124] was granted by the patent office on 2019-07-30 for 2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides.
This patent grant is currently assigned to BAYER CROPSCIENCE AKTIENGESELLSCHAFT. The grantee listed for this patent is BAYER CROPSCIENCE AKTIENGESELLSCHAFT. Invention is credited to Bernd Alig, Alexander Arlt, Rudiger Fischer, Ulrich Gorgens, Kerstin Ilg, Jun Li, Olga Malsam, Andreas Turberg, Sergey Zhersh.
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United States Patent |
10,364,243 |
Fischer , et al. |
July 30, 2019 |
2-(het)aryl-substituted fused bicyclic heterocycle derivatives as
pesticides
Abstract
The invention relates to novel compounds of the formula (I)
##STR00001## in which the R.sup.1, R.sup.2a, R.sup.2b, R.sup.3,
A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and n radicals are each
as defined above, to the use thereof as acaricides and/or
insecticides for controlling animal pests and to processes and
intermediates for preparation thereof.
Inventors: |
Fischer; Rudiger (Pulheim,
DE), Alig; Bernd (Konigswinter, DE), Ilg;
Kerstin (Koln, DE), Malsam; Olga (Rosrath,
DE), Gorgens; Ulrich (Ratingen, DE),
Turberg; Andreas (Haan, DE), Li; Jun (Hannover,
DE), Zhersh; Sergey (Brovary, UA), Arlt;
Alexander (Leverkusen, DE) |
Applicant: |
Name |
City |
State |
Country |
Type |
BAYER CROPSCIENCE AKTIENGESELLSCHAFT |
Monheim am Rhein |
N/A |
DE |
|
|
Assignee: |
BAYER CROPSCIENCE
AKTIENGESELLSCHAFT (Monheim am Rhein, DE)
|
Family
ID: |
50101813 |
Appl.
No.: |
15/119,124 |
Filed: |
February 5, 2015 |
PCT
Filed: |
February 05, 2015 |
PCT No.: |
PCT/EP2015/052351 |
371(c)(1),(2),(4) Date: |
August 15, 2016 |
PCT
Pub. No.: |
WO2015/121136 |
PCT
Pub. Date: |
August 20, 2015 |
Prior Publication Data
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Document
Identifier |
Publication Date |
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US 20170073342 A1 |
Mar 16, 2017 |
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Foreign Application Priority Data
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|
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Feb 17, 2014 [EP] |
|
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14155372 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07D
471/04 (20130101); C07D 487/04 (20130101); A01N
43/90 (20130101); A61P 33/00 (20180101); C07D
473/40 (20130101); C07D 498/04 (20130101); C07D
213/74 (20130101); C07D 213/73 (20130101) |
Current International
Class: |
C07D
471/04 (20060101); A01N 43/90 (20060101); C07D
213/73 (20060101); C07D 213/74 (20060101); C07D
473/40 (20060101); C07D 498/04 (20060101); C07D
487/04 (20060101) |
Foreign Patent Documents
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0 079 083 |
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May 1983 |
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EP |
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2004037823 |
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May 2004 |
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WO |
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2012/086848 |
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Jun 2012 |
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WO |
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2013/018928 |
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Feb 2013 |
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WO |
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2015/000715 |
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Jan 2015 |
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WO |
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WO-2015000715 |
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Jan 2015 |
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WO |
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2016/116338 |
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Jul 2016 |
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WO |
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WO-2016116338 |
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Jul 2016 |
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WO |
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Other References
American Chemical Society. STN Database. .COPYRGT. Jan. 15, 2015.
RN 1643138-99-1. cited by examiner .
International Search Report of PCT/EP2015/052351 dated Mar. 9,
2015. cited by applicant.
|
Primary Examiner: Kosar; Andrew D
Assistant Examiner: Kenyon; John S
Attorney, Agent or Firm: McBee Moore Woodward & Vanik
IP, LLC
Claims
The invention claimed is:
1. A compound of formula (I) ##STR00062## in which A.sup.1 is
nitrogen, A.sup.2 is --N--R.sup.5, A.sup.3 is oxygen, A.sup.4 is
.dbd.C--R.sup.4, A.sup.5 is .dbd.C--H, R.sup.1 is
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyloxy-(C.sub.1-C.sub.6)alkyl,(C.sub.2-C.sub.6)h-
aloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, amino,
(C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino,
(C.sub.3-C.sub.8)cycloalkylamino,
(C.sub.1-C.sub.6)alkylcarbonylamino,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl-
,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6-
)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C-
.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonylamino,
aminosulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl-(C.sub.1-C.sub.6)alkyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl-(C.sub.1-C.sub.6)alkyl, or
is (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.3-C.sub.8)cycloalkyl, each of which is optionally mono- or
polysubstituted identically or differently by aryl, hetaryl or
heterocyclyl, where aryl, hetaryl or heterocyclyl may each
independently optionally be mono- or polysubstituted identically or
differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl,
carbamoyl, aminosulphonyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphonyl, (C.sub.1-C.sub.6)alkylsulphimino,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylsulphoximino,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.3-C.sub.6)trialkylsilyl or benzyl, or R.sup.1 is aryl,
hetaryl or heterocyclyl, each of which is optionally mono- or
polysubstituted identically or differently by halogen, cyano,
nitro, hydroxyl, amino, carboxyl, carbamoyl,
(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)alkylthio,(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphonyl, (C.sub.1-C.sub.6)alkylsulphimino,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylsulphoximino,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.3-C.sub.6)trialkylsilyl, (.dbd.O) (only in the case of
heterocyclyl) or (.dbd.O).sub.2 (only in the case of heterocyclyl),
R.sup.2a, R.sup.2b, R.sup.3 and R.sup.4 are each independently
hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,
tri-(C.sub.1-C.sub.6)alkylsilyl, (C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl,
(C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylthiocarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, NHCO--(C.sub.1-C.sub.6)alkyl
((C.sub.1-C.sub.6)alkylcarbonylamino), or R.sup.2a, R.sup.2b,
R.sup.3, R.sup.4 are each independently aryl or hetaryl, each of
which is optionally mono- or polysubstituted identically or
differently, where (in the case of hetaryl) at least one carbonyl
group may optionally be present and/or where possible substituents
in each case are as follows: cyano, carboxyl, halogen, nitro,
acetyl, hydroxyl, amino, SCN, tri-(C.sub.1-C.sub.6)alkylsilyl,
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, R.sup.5 is
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl-
,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6-
)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C-
.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
aminocarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylamino-(C.sub.1-C.sub.6)alkyl,
di(C.sub.1-C.sub.6)alkylamino-(C.sub.1-C.sub.6)alkyl or
(C.sub.3-C.sub.8)cycloalkylamino-(C.sub.1-C.sub.6)alkyl, n is 0, 1
or 2, with the proviso that the compound of formula (I) is not a
compound in which the variables are defined as follows:
TABLE-US-00004 A.sup.1 A.sup.2 A.sup.3 A.sup.4 A.sup.5 N N-methyl O
.dbd.C--H .dbd.C--H N N-methyl O .dbd.C--H .dbd.C--H N N-methyl O
.dbd.C--H .dbd.C--H N N-methyl O .dbd.C--H .dbd.C--H N N-methyl O
.dbd.C--H .dbd.C--H R.sup.1 n R.sup.3 R.sup.2a R.sup.2b
C.sub.2H.sub.5 2 CF.sub.3 H H C.sub.2H.sub.5 2 CF.sub.3 CF.sub.3 H
CH.sub.3 2 CF.sub.3 CF.sub.3 H C.sub.2H.sub.5 2 CF.sub.3 OCHF.sub.2
H C.sub.2H.sub.5 2 Br CF.sub.3 H.
2. The compound of formula (I) according to claim 1 in which
A.sup.1 is nitrogen, A.sup.2 is --N--R.sup.5, A.sup.3 is oxygen,
A.sup.4 is .dbd.C--R.sup.4, A.sup.5 is .dbd.C--H, R.sup.1 is
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)cyanoalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl,
(C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)alkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.6)cycloalkylamino,
(C.sub.1-C.sub.4)alkylcarbonylamino,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylcarbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, or is (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkynyl, (C.sub.3-C.sub.6)cycloalkyl, each of
which is optionally mono- or disubstituted identically or
differently by aryl, hetaryl or heterocyclyl, where aryl, hetaryl
and heterocyclyl may each optionally be mono- or disubstituted
identically or differently by halogen, cyano, carbamoyl,
aminosulphonyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.4)cycloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)alkylsulphimino,
or R.sup.1 is aryl, hetaryl or heterocyclyl, each of which is
optionally mono- or disubstituted identically or differently by
halogen, cyano, carbamoyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)-alkoxy,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)alkylsulphimino,
(C.sub.1-C.sub.4)alkylsulphoximino, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.3-C.sub.4)trialkylsilyl, (.dbd.O) (only in the case of
heterocyclyl) or (.dbd.O).sub.2 (only in the case of heterocyclyl),
R.sup.2a, R.sup.2b, R.sup.3 and R.sup.4 are each independently
hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,
tri-(C.sub.1-C.sub.4)alkylsilyl, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)cyanoalkyl,
(C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)cyanoalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
aminothiocarbonyl, (C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di(C.sub.1-C.sub.4)alkylaminosulphonyl, aminothiocarbonyl,
NHCO--(C.sub.1-C.sub.4)alkyl ((C.sub.1-C.sub.4)alkylcarbonylamino),
or R.sup.2a, R.sup.2b, R.sup.3 and R.sup.4 are each independently
phenyl or hetaryl, each of which is mono- or disubstituted
identically or differently, where (in the case of hetaryl) at least
one carbonyl group may optionally be present and/or where possible
substituents in each case are as follows: cyano, halogen, nitro,
acetyl, amino, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)cyanoalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di(C.sub.1-C.sub.4)alkylaminosulphonyl, R.sup.5 is
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl,
(C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)alkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl-
, (C.sub.1-C.sub.4)alkylcarbonyl-(C.sub.1-C.sub.4)alkyl, n is 0, 1
or 2.
3. The compound of the formula (I) according to claim 1 in which
A.sup.1 is nitrogen, A.sup.2 is --N--R.sup.5, A.sup.3 is oxygen,
A.sup.4 is .dbd.C--R.sup.4, A.sup.5 is .dbd.C--H, R.sup.1 is
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl, or is
(C.sub.1-C.sub.4)alkyl optionally monosubstituted by phenyl,
pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl,
thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl,
where phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl,
pyrazolyl, triazolyl, thiazolyl, tetrazolyl, piperazinyl,
tetrahydrofuryl or oxetanyl may each optionally be mono- or
disubstituted identically or differently by halogen,
(C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)haloalkyl, or R.sup.1 is
phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl,
triazolyl, thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl or
oxetanyl, each of which is optionally mono- or disubstituted
identically or differently by halogen, (C.sub.1-C.sub.4)alkyl or
(C.sub.1-C.sub.4)haloalkyl, R.sup.2a is hydrogen, cyano,
aminocarbonyl, halogen, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)haloalkylsulphinyl or
(C.sub.1-C.sub.4)haloalkylsulphonyl, R.sup.2b is hydrogen,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkyl,
NHCO--(C.sub.1-C.sub.4)alkyl or halogen, R.sup.3 is hydrogen,
halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulphinyl, (C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl, or is phenyl, pyrazolyl or
imidazolyl, each of which is optionally monosubstituted by
trifluoromethyl, R.sup.4 is hydrogen, halogen, cyano or
(C.sub.1-C.sub.3)alkyl, R.sup.5 is (C.sub.1-C.sub.4)alkyl or
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl, n is 0, 1 or 2.
4. The compound of the formula (I) according to claim 1 in which
A.sup.1 is nitrogen, A.sup.2 is --N--R.sup.5, A.sup.3 is oxygen,
A.sup.4 is .dbd.C--H, A.sup.5 is .dbd.C--H, R.sup.1 is methyl,
ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl,
tert-butyl, cyclobutyl, hydroxyethyl (--CH.sub.2--CH.sub.2--OH),
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
--(CH.sub.2).sub.2--S--C.sub.2H.sub.5,
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 or ##STR00063##
R.sup.2a is hydrogen, cyano, aminocarbonyl (CONH.sub.2),
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,
trifluoromethylthio, trifluoromethylsulphonyl,
trifluoromethylsulphinyl, fluorine or chlorine, R.sup.2b is
hydrogen, methoxy, ethoxy, trifluoromethyl, methylcarbonylamino
(NHCO-methyl), fluorine or chlorine, R.sup.3 is fluorine, chlorine,
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,
trifluoromethylthio, trifluoromethylsulphonyl,
trifluoromethylsulphinyl, or is phenyl, pyrazol-1-yl or
imidazol-1-yl, each of which is optionally monosubstituted by
trifluoromethyl, R.sup.4 is hydrogen, fluorine, chlorine, bromine
or cyano, R.sup.5 is methyl, ethyl, i-propyl, methoxymethyl or
methoxyethyl, n is 0, 1 or 2.
5. The compound of the formula (I) according to claim 1 in which
A.sup.1 is nitrogen (N), A.sup.2 is --N--CH.sub.3, A.sup.3 is
oxygen, A.sup.4 is .dbd.C--H, A.sup.5 is .dbd.C--H, R.sup.1 is
methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl,
tert-butyl, cyclobutyl, hydroxyethyl (--CH.sub.2--CH.sub.2--OH),
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
--(CH.sub.2).sub.2--S--C.sub.2H.sub.5,
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 or ##STR00064##
(oxetan-3-yl), R.sup.2a is hydrogen, cyano, aminocarbonyl
(CONH.sub.2), fluoromethyl, difluoromethyl, trifluoromethyl,
fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl,
pentafluoroethyl, trifluoromethoxy, trifluoromethylthio,
trifluoromethylsulphonyl, trifluoromethylsulphinyl, fluorine or
chlorine, R.sup.2b is hydrogen, methoxy, ethoxy, trifluoromethyl,
methylcarbonylamino (NHCO-methyl), fluorine or chlorine, R.sup.3 is
fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl,
fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl,
pentafluoroethyl, trifluoromethoxy, trifluoromethylthio,
trifluoromethylsulphonyl, trifluoromethylsulphinyl, or is phenyl,
##STR00065## (pyrazol-1-yl) or ##STR00066## (imidazol-1-yl), each
of which is optionally monosubstituted by trifluoromethyl, n is 0,
1 or 2.
6. The compound of the formula (I) according to claim 1 in which
A.sup.1 is nitrogen (N), A.sup.2 is --N--CH.sub.3, A.sup.3 is
oxygen, A.sup.4 is .dbd.C--H, A.sup.5 is .dbd.C--H, R.sup.1 is
methyl, ethyl, n-propyl, i-propyl, trifluoromethyl,
--CH.sub.2--CH.sub.2--F, --CH.sub.2--CH.sub.2--OH,
--(CH.sub.2).sub.2--S--C.sub.2H.sub.5,
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 or ##STR00067##
R.sup.2a is hydrogen, trifluoromethyl, cyano, CONH.sub.2, fluorine
or chlorine, R.sup.2b is hydrogen, chlorine, trifluoromethyl,
methoxy or NHCOCH.sub.3, R.sup.3 is pentafluoroethyl,
trifluoromethyl, chlorine, 4-CF.sub.3(C.sub.6H.sub.4),
4-(CF.sub.3)pyrazol-1-yl, 3-(CF.sub.3)pyrazol-1-yl or
4-(CF.sub.3)imidazol-1-yl, n is 0, 1 or 2.
7. The compound of the formula (I) according to claim 1, wherein
R.sup.2b is acetyl, amino, SCN, tri-(C.sub.1-C.sub.6)alkylsilyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl,
(C.sub.2-C.sub.6)cyanoalkynyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylthiocarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di-(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di-(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di-(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, NHCO--(C.sub.1-C.sub.6)alkyl
((C.sub.1-C.sub.6)alkylcarbonylamino), is in each case optionally
singly or multiply, identically or differently substituted hetaryl,
where at least one carbonyl group may optionally be present and/or
where possible substituents in each case are as follows: cyano,
carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,
tri-(C.sub.1-C.sub.6)alkylsilyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl,
(C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di-(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di-(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di-(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino.
8. The compound of the formula (I) according to claim 1, wherein
R.sup.2b is acetyl, amino, SCN, tri-(C.sub.1-C.sub.4)alkylsilyl,
(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl,
(C.sub.2-C.sub.4)alkynyl, (C.sub.2-C.sub.4)haloalkynyl,
(C.sub.2-C.sub.4)cyanoalkynyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
aminothiocarbonyl, (C.sub.1-C.sub.4)alkylaminocarbonyl,
di-(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di-(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di-(C.sub.1-C.sub.4)alkylaminosulphonyl, aminothiocarbonyl,
NHCO--(C.sub.1-C.sub.4)alkyl ((C.sub.1-C.sub.4)alkylcarbonylamino),
is in each case singly or doubly, identically or differently
substituted hetaryl, where at least one carbonyl group may
optionally be present and/or where possible substituents in each
case are as follows: cyano, halogen, nitro, acetyl, amino,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)cyanoalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
(C.sub.1-C.sub.4)alkylaminocarbonyl,
di-(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di-(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di-(C.sub.1-C.sub.4)alkylaminosulphonyl.
9. The compound of the formula (I) according to claim 1, wherein
R.sup.2b is (C.sub.1-C.sub.4)alkoxy or
NHCO--(C.sub.1-C.sub.4)alkyl.
10. The compound of the formula (I) according to claim 1, wherein
R.sup.2b is methoxy, ethoxy or NHCO-methyl.
11. The compound of the formula (I) according to claim 1, wherein
R.sup.2b is methoxy or NHCOCH.sub.3.
12. A composition comprising a content of at least one compound of
the formula (I) according to claim 1 and one or more customary
extenders and/or surfactants.
13. A method for controlling pests, comprising allowing a compound
of the formula (I) according to claim 1 to act on the pests and/or
a habitat thereof.
14. A compound of the formula (I) ##STR00068## wherein A.sup.1 is
nitrogen, A.sup.2 is N-methyl, A.sup.3 is oxygen, A.sup.4 is
nitrogen, A.sup.5 is CH, R.sup.1 is C.sub.2H.sub.5, R.sup.2a is
CF.sub.3, R.sup.2b is H, R.sup.3 is CF.sub.3, and n is 0.
15. The compound of the formula (I) according to claim 1, wherein
the variables are defined as follows: TABLE-US-00005 A.sup.1
A.sup.2 A.sup.3 A.sup.4 A.sup.5 R.sup.1 n R.sup.3 R.sup.2a R.sup.2-
b N N-methyl O CH CH --(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 2
CF.sub.3- CF.sub.3 H N N-methyl O CH CH i-C.sub.3H.sub.7 1 CF.sub.3
CF.sub.3 H N N-methyl O CH CH i-C.sub.3H.sub.7 2 CF.sub.3 CF.sub.3
H N N-methyl O CH CH --(CH.sub.2).sub.2--S--C.sub.2H.sub.5 0
CF.sub.3 CF.sub- .3 H N N-methyl O CH CH CF.sub.3 0 CF.sub.3 H H N
N-methyl O CH CH n-C.sub.3H.sub.7 0 CF.sub.3 CF.sub.3 H N N-methyl
O CH CH n-C.sub.3H.sub.7 2 CF.sub.3 CF.sub.3 H N N-methyl O CH CH
n-C.sub.3H.sub.7 1 CF.sub.3 CF.sub.3 H N N-methyl O CH CH
i-C.sub.3H.sub.7 0 CF.sub.3 CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 2 CF.sub.3 H 5-OMe N N-methyl O CH CH C.sub.2H.sub.5
0 C.sub.2F.sub.5 H H N N-methyl O CH CH C.sub.2H.sub.5 0
C.sub.2F.sub.5 CF.sub.3 H N N-methyl O CH CH C.sub.2H.sub.5 2
CF.sub.3 H 3-CF.sub.3 N N-methyl O CH CH C.sub.2H.sub.5 2 CF.sub.3
H 5-NHCOMe N N-methyl O CH CH C.sub.2H.sub.5 0 CF.sub.3 H 5-NHCOMe
N N-methyl O CH CH C.sub.2H.sub.5 1 CF.sub.3 H 3-CF.sub.3 N
N-methyl O CH CH C.sub.2H.sub.5 2 Cl CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 0 CF.sub.3 H 5-OMe N N-methyl O CH CH
CH.sub.2--CH.sub.2F 2 CF.sub.3 CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 0 Cl CF.sub.3 H N N-methyl O CH CH C.sub.2H.sub.5 2
CF.sub.3 CONH.sub.2 H N N-methyl O CH CH CH.sub.2--CH.sub.2F 2
CF.sub.3 CF.sub.3 H N N-methyl O CH CH CH.sub.2--CH.sub.2OH 2
CF.sub.3 CF.sub.3 H N N-methyl O CH CH CH.sub.2--CH.sub.2OH 0
CF.sub.3 CF.sub.3 H N N-methyl O CH CH C.sub.2H.sub.5 0 CF.sub.3
CONH.sub.2 H N N-methyl O CH CH C.sub.2H.sub.5 1 C.sub.2F.sub.5 H H
N N-methyl O CH CH C.sub.2H.sub.5 1 C.sub.2F.sub.5 CF.sub.3 H N
N-methyl O CH CH C.sub.2H.sub.5 0 4-CF.sub.3(C.sub.6H.sub.4)
CF.sub.3 H N N-methyl O CH CH C.sub.2H.sub.5 0
4-(CF.sub.3)pyrazol-1-y1 CF.sub.3 H N N-methyl O CH CH
n-C.sub.3H.sub.7 0 CF.sub.3 H 5-OMe N N-methyl O CH CH CH3 0
CF.sub.3 H 5-OMe N N-methyl O CH CH C.sub.2H.sub.5 2 C.sub.2F.sub.5
H H N N-methyl O CH CH C.sub.2H.sub.5 0 3-(CF.sub.3)pyrazol-1-y1
CF.sub.3 H N N-methyl O CH CH C.sub.2H.sub.5 0 CF.sub.3 H
3-CF.sub.3 N N-methyl O CH CH n-C.sub.3H.sub.7 2 CF.sub.3 H 5-OMe N
N-methyl O CH CH C.sub.2H.sub.5 2 CF.sub.3 CN H N N-methyl O CH CH
CH.sub.3 2 CF.sub.3 H 5-OMe N N-methyl O CH CH C.sub.2H.sub.5 0
4-(CF.sub.3)imidazol-1-yl CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 2 4-(CF.sub.3)imidazol-1-yl CF.sub.3 H N N-methyl O
CH CH C.sub.2H.sub.5 2 4-(CF.sub.3)pyrazol-1-y1 CF.sub.3 H N
N-methyl O CH CH C.sub.2H.sub.5 2 3-(CF.sub.3)pyrazol-1-y1 CF.sub.3
H.
16. The compound of the formula (I) according to claim 1, wherein
the variables are defined as follows: TABLE-US-00006 A.sup.1
A.sup.2 A.sup.3 A.sup.4 A.sup.5 N N-methyl O CH CH N N-methyl O CH
CH N N-methyl O CH CH N N-methyl O CH CH N N-methyl O CH CH N
N-methyl O CH CH N N-methyl O CH CH N N-methyl O CH CH N N-methyl O
CH CH R.sup.1 n R.sup.3 R.sup.2a R.sup.2b
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 2 CF.sub.3 CF.sub.3 H
i-C.sub.3H.sub.7 1 CF.sub.3 CF.sub.3 H i-C.sub.3H.sub.7 2 CF.sub.3
CF.sub.3 H --(CH.sub.2).sub.2--S--C.sub.2H.sub.5 0 CF.sub.3
CF.sub.3 H CF.sub.3 0 CF.sub.3 H H n-C.sub.3H.sub.7 0 CF.sub.3
CF.sub.3 H n-C.sub.3H.sub.7 2 CF.sub.3 CF.sub.3 H n-C.sub.3H.sub.7
1 CF.sub.3 CF.sub.3 H i-C.sub.3H.sub.7 0 CF.sub.3 CF.sub.3 H.
17. The compound of the formula (I) according to claim 1, wherein
the variables are defined as follows: TABLE-US-00007 A.sup.1
A.sup.2 A.sup.3 A.sup.4 A.sup.5 R.sup.1 n R.sup.3 R.sup.2a R.sup.2-
b N N-methyl O CH CH C.sub.2H.sub.5 2 CF.sub.3 H 5-OMe N N-methyl O
CH CH C.sub.2H.sub.5 0 C.sub.2F.sub.5 H H N N-methyl O CH CH
C.sub.2H.sub.5 0 C.sub.2F.sub.5 CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 2 CF.sub.3 H 3-CF.sub.3 N N-methyl O CH CH
C.sub.2H.sub.5 2 CF.sub.3 H 5-NHCOMe N N-methyl O CH CH
C.sub.2H.sub.5 0 CF.sub.3 H 5-NHCOMe N N-methyl O CH CH
C.sub.2H.sub.5 1 CF.sub.3 H 3-CF.sub.3 N N-methyl O CH CH
C.sub.2H.sub.5 2 Cl CF.sub.3 H N N-methyl O CH CH C.sub.2H.sub.5 0
CF.sub.3 H 5-OMe N N-methyl O CH CH CH.sub.2--CH.sub.2F 2 CF.sub.3
CF.sub.3 H N N-methyl O CH CH C.sub.2H.sub.5 0 Cl CF.sub.3 H N
N-methyl O CH CH C.sub.2H.sub.5 2 CF.sub.3 CONH.sub.2 H N N-methyl
O CH CH CH.sub.2--CH.sub.2F 2 CF.sub.3 CF.sub.3 H N N-methyl O CH
CH CH.sub.2--CH.sub.2OH 2 CF.sub.3 CF.sub.3 H N N-methyl O CH CH
CH.sub.2--CH.sub.2OH 0 CF.sub.3 CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 0 CF.sub.3 CONH.sub.2 H N N-methyl O CH CH
C.sub.2H.sub.5 1 C.sub.2F.sub.5 H H N N-methyl O CH CH
C.sub.2H.sub.5 1 C.sub.2F.sub.5 CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 0 4-CF.sub.3(C.sub.6H.sub.4) CF.sub.3 H N N-methyl O
CH CH C.sub.2H.sub.5 0 4-(CF.sub.3)pyrazol-1-y1 CF.sub.3 H N
N-methyl O CH CH n-C.sub.3H.sub.7 0 CF.sub.3 H 5-OMe N N-methyl O
CH CH CH.sub.3 0 CF.sub.3 H 5-OMe N N-methyl O CH CH C.sub.2H.sub.5
2 C.sub.2F.sub.5 H H N N-methyl O CH CH C.sub.2H.sub.5 0
3-(CF.sub.3)pyrazol-1-y1 CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 0 CF.sub.3 H 3-CF.sub.3 N N-methyl O CH CH
n-C.sub.3H.sub.7 2 CF.sub.3 H 5-OMe N N-methyl O CH CH
C.sub.2H.sub.5 2 CF.sub.3 CN H N N-methyl O CH CH CH.sub.3 2
CF.sub.3 H 5-OMe N N-methyl O CH CH C.sub.2H.sub.5 0
4-(CF.sub.3)imidazol-1-yl CF.sub.3 H N N-methyl O CH CH
C.sub.2H.sub.5 2 4-(CF.sub.3)imidazol-1-yl CF.sub.3 H N N-methyl O
CH CH C.sub.2H.sub.5 2 4-(CF.sub.3)pyrazol-1-y1 CF.sub.3 H N
N-methyl O CH CH C.sub.2H.sub.5 2 3-(CF.sub.3)pyrazol-1-y1 CF.sub.3
H.
18. The compound of the formula (I) according to claim 1 in which
R.sup.1 is (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl, or is
(C.sub.1-C.sub.4)alkyl monosubstituted by phenyl, pyridyl,
pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl, thiazolyl,
tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl, where phenyl,
pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl,
thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl may
each optionally be mono- or disubstituted identically or
differently by halogen, (C.sub.1-C.sub.4)alkyl or
(C.sub.1-C.sub.4)haloalkyl, or R.sup.1 is phenyl, pyridyl,
pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl, thiazolyl,
tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl, each of which
is optionally mono- or disubstituted identically or differently by
halogen, (C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)haloalkyl.
19. The compound of the formula (I) according to claim 1 in which
R.sup.3 is hydrogen, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulphinyl, (C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl, or is phenyl, pyrazolyl or
imidazolyl, each of which is optionally monosubstituted by
trifluoromethyl.
20. The compound of the formula (I) according to claim 1 in which
R.sup.2a is cyano, aminocarbonyl, halogen, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulphinyl, (C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)haloalkylsulphinyl
or (C.sub.1-C.sub.4)haloalkylsulphonyl.
21. The compound of the formula (I) according to claim 1 in which
R.sub.2b is methoxy, ethoxy, trifluoromethyl, methylcarbonylamino
(NHCO-methyl), fluorine or chlorine.
22. A compound of formula (I) ##STR00069## in which A.sup.1 is
nitrogen, A.sup.2 is --N--R.sup.5, A.sup.3 is oxygen, A.sup.4 is
.dbd.C--R.sup.4, A.sup.5 is .dbd.C--H, R.sup.1 is
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, amino,
(C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino,
(C.sub.3-C.sub.8)cycloalkylamino,
(C.sub.1-C.sub.6)alkylcarbonylamino,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl-
,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6-
)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C-
.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonylamino,
aminosulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl-(C.sub.1-C.sub.6)alkyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl-(C.sub.1-C.sub.6)alkyl, or
is (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.3-C.sub.8)cycloalkyl, each of which is optionally mono- or
polysubstituted identically or differently by aryl, hetaryl or
heterocyclyl, where aryl, hetaryl or heterocyclyl may each
independently optionally be mono- or polysubstituted identically or
differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl,
carbamoyl, aminosulphonyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphonyl, (C.sub.1-C.sub.6)alkylsulphimino,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylsulphoximino,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.3-C.sub.6)trialkylsilyl or benzyl, or R.sup.1 is aryl,
hetaryl or heterocyclyl, each of which is optionally mono- or
polysubstituted identically or differently by halogen, cyano,
nitro, hydroxyl, amino, carboxyl, carbamoyl,
(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylsulphinyl, (C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphimino,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylsulphoximino,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.3-C.sub.6)trialkylsilyl, (.dbd.O) (only in the case of
heterocyclyl) or (.dbd.O).sub.2 (only in the case of heterocyclyl),
R.sub.2a, R.sup.2b, R.sup.3 and R.sup.4 are each independently
hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,
tri-(C.sub.1-C.sub.6)alkylsilyl, (C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl,
(C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylthiocarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, NHCO--(C.sub.1-C.sub.6)alkyl
((C.sub.1-C.sub.6)alkylcarbonylamino), or R.sup.2a , R.sup.2b,
R.sup.3 and R.sup.4 are each independently aryl or hetaryl, each of
which is optionally mono- or polysubstituted identically or
differently, where (in the case of hetaryl) at least one carbonyl
group may optionally be present and/or where possible substituents
in each case are as follows: cyano, carboxyl, halogen, nitro,
acetyl, hydroxyl, amino, SCN, tri-(C.sub.1-C.sub.6)alkylsilyl,
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, R.sup.5 is
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl.sub.4C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl-
,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6-
)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C-
.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
aminocarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylamino-(C.sub.1-C.sub.6)alkyl,
di(C.sub.1-C.sub.6)alkylamino-(C.sub.1-C.sub.6)alkyl or
(C.sub.3-C.sub.8)cycloalkylamino-(C.sub.1-C.sub.6)alkyl, n is 0, 1
or 2, wherein when R.sup.3 is CF.sub.3, R.sup.4 is H, R.sup.5 is
CH.sub.3, R.sup.2b is H, and R.sup.1 is CH.sub.3 or
CH.sub.2CH.sub.3, then R.sup.2a is not H, CF.sub.3, Br, or Cl; and
wherein when R.sup.3 is CF.sub.3, R.sup.4 is H, R.sup.5 is
CH.sub.3, R.sup.2b is 3-CH.sub.3, and R.sup.1 is CH.sub.2CH.sub.3,
then R.sup.2a is not H, CF.sub.3, Br, or Cl.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a National Stage entry of International
Application No. PCT/EP2015/052351, filed Feb. 5, 2015, which claims
priority to European Patent Application No. 14155372.7, filed Feb.
17, 2014. The disclosures of the priority applications are
incorporated in their entirety herein by reference.
BACKGROUND
Field of the Invention
The present invention relates to novel 2-(het)aryl-substituted
fused bicyclic heterocycle derivatives of the formula (I), to the
use thereof as acaricides and/or insecticides for controlling
animal pests, particularly arthropods and especially insects and
arachnids, and to processes and intermediates for preparation
thereof.
Description of Related Art
2-(Het)aryl-substituted fused bicyclic heterocycle derivatives
having insecticidal properties have already been described in the
literature, for example in WO 2010/125985, WO 2012/074135, WO
2012/086848, WO 2013/018928, WO 2014/142292 and WO 2014/148451, and
also WO 2015/000715.
However, the active ingredients already known according to the
documents cited above have some disadvantages on application,
whether because they exhibit only a narrow range of application or
because they do not have satisfactory insecticidal or acaricidal
activity.
SUMMARY
Novel 2-(het)aryl-substituted fused bicyclic heterocycle
derivatives have now been found, and these have advantages over the
compounds already known, examples of which are better biological or
environmental properties, a wider range of application methods,
better insecticidal or acaricidal activity, and also good
compatibility with crop plants. The 2-(het)aryl-substituted fused
bicyclic heterocycle derivatives can be used in combination with
further agents for improving efficacy, especially against insects
that are difficult to control.
The present invention therefore provides novel compounds of the
formula (I)
##STR00002## in which A.sup.1 is nitrogen, .dbd.N.sup.+--O.sup.- or
.dbd.C--R.sup.4, A.sup.2 is --N--R.sup.5, oxygen or sulphur,
A.sup.3 is oxygen, .dbd.N--H or .dbd.N--CN, A.sup.4 is nitrogen,
.dbd.N.sup.+--O.sup.- or .dbd.C--R.sup.4, A.sup.5 is nitrogen,
.dbd.N.sup.+--O.sup.- or .dbd.C--R.sup.4, R.sup.1 is
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, amino,
(C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino,
(C.sub.3-C.sub.8)cycloalkylamino,
(C.sub.1-C.sub.6)alkylcarbonylamino,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl-
,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6-
)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C-
.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonylamino,
aminosulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl-(C.sub.1-C.sub.6)alkyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl-(C.sub.1-C.sub.6)alkyl, or
is (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.3-C.sub.8)cycloalkyl, each of which is mono- or
polysubstituted identically or differently by aryl, hetaryl or
heterocyclyl, where aryl, hetaryl or heterocyclyl may each
independently be mono- or polysubstituted identically or
differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl,
carbamoyl, aminosulphonyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphonyl, (C.sub.1-C.sub.6)alkylsulphimino,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylsulphoximino,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.3-C.sub.6)trialkylsilyl or benzyl, or R.sup.1 is aryl,
hetaryl or heterocyclyl, each of which is mono- or polysubstituted
identically or differently by halogen, cyano, nitro, hydroxyl,
amino, carboxyl, carbamoyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphonyl, (C.sub.1-C.sub.6)alkylsulphimino,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylsulphoximino,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.3-C.sub.6)trialkylsilyl, (.dbd.O) (only in the case of
heterocyclyl) or (.dbd.O).sub.2 (only in the case of heterocyclyl),
R.sup.2a, R.sup.2b, R.sup.3 and R.sup.4 are each independently
hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,
tri-(C.sub.1-C.sub.6)alkylsilyl, (C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl,
(C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylthiocarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, is aryl or hetaryl, each of which
is mono- or polysubstituted identically or differently, where (in
the case of hetaryl) at least one carbonyl group may optionally be
present and/or where possible substituents in each case are as
follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino,
SCN, tri-(C.sub.1-C.sub.6)alkylsilyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl,
(C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, R.sup.5 is
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl-
,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6-
)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C-
.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
aminocarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylamino-(C.sub.1-C.sub.6)alkyl,
di(C.sub.1-C.sub.6)alkylamino-(C.sub.1-C.sub.6)alkyl or
(C.sub.3-C.sub.8)cycloalkylamino-(C.sub.1-C.sub.6)alkyl, n is 0, 1
or 2, where, in the case that n=2, the meanings of A.sup.3 may be
the same or different.
It has additionally been found that the compounds of the formula
(I) have very good efficacy as pesticides, preferably as
insecticides and/or acaricides, and additionally generally have
very good plant compatibility, especially with respect to crop
plants.
DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT
The inventive compounds are defined in general terms by the formula
(I). Preferred substituents or ranges of the radicals given in the
formulae mentioned above and below are illustrated hereinafter:
A.sup.1 is preferably nitrogen, .dbd.N.sup.+--O.sup.- or
.dbd.C--R.sup.4, A.sup.2 is preferably --N--R.sup.5, oxygen or
sulphur, A.sup.3 is preferably oxygen, .dbd.N--H or .dbd.N--CN,
A.sup.4 is preferably nitrogen, .dbd.N.sup.+--O.sup.- or
.dbd.C--R.sup.4, A.sup.5 is preferably nitrogen,
.dbd.N.sup.+--O.sup.- or .dbd.C--R.sup.4, R.sup.1 is preferably
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl,
(C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)alkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.6)cycloalkylamino,
(C.sub.1-C.sub.4)alkylcarbonylamino,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylcarbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, or is (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkynyl, (C.sub.3-C.sub.6)cycloalkyl, each of
which is optionally mono- or disubstituted identically or
differently by aryl, hetaryl or heterocyclyl, where aryl, hetaryl
and heterocyclyl may each optionally be mono- or disubstituted
identically or differently by halogen, cyano, carbamoyl,
aminosulphonyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.4)cycloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)alkylsulphimino,
or R.sup.1 is preferably aryl, hetaryl or heterocyclyl, each of
which is optionally mono- or disubstituted identically or
differently by halogen, cyano, carbamoyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)-alkoxy,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)alkylsulphimino,
(C.sub.1-C.sub.4)alkylsulphoximino, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.3-C.sub.4)trialkylsilyl, (.dbd.O) (only in the case of
heterocyclyl) or (.dbd.O).sub.2 (only in the case of heterocyclyl),
R.sup.2a, R.sup.2b, R.sup.3 and R.sup.4 are preferably each
independently hydrogen, cyano, halogen, nitro, acetyl, hydroxyl,
amino, SCN, tri-(C.sub.1-C.sub.4)alkylsilyl,
(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)cyanoalkyl,
(C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)cyanoalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
aminothiocarbonyl, (C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di(C.sub.1-C.sub.4)alkylaminosulphonyl, aminothiocarbonyl, is
phenyl or hetaryl, each of which is mono- or disubstituted
identically or differently, where (in the case of hetaryl) at least
one carbonyl group may optionally be present and/or where possible
substituents in each case are as follows: cyano, halogen, nitro,
acetyl, amino, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)cyanoalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di(C.sub.1-C.sub.4)alkylaminosulphonyl, R.sup.5 is preferably
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl,
(C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)alkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl-
, (C.sub.1-C.sub.4)alkylcarbonyl-(C.sub.1-C.sub.4)alkyl, n is
preferably 0, 1 or 2, where, in the case that n=2, the meanings of
A.sup.3 may be the same or different. A.sup.1 is more preferably
nitrogen or .dbd.C--R.sup.4, A.sup.2 is more preferably
--N--R.sup.5 or oxygen, A.sup.3 is more preferably oxygen or
.dbd.N--H, A.sup.4 is more preferably nitrogen or .dbd.C--R.sup.4,
A.sup.5 is more preferably nitrogen or .dbd.C--R.sup.4, R.sup.1 is
more preferably (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)alkynyl, (C.sub.2-C.sub.4)haloalkynyl,
(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl, or is
(C.sub.1-C.sub.4)alkyl optionally monosubstituted by phenyl,
pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl,
thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl,
where phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl,
pyrazolyl, triazolyl, thiazolyl, tetrazolyl, piperazinyl,
tetrahydrofuryl or oxetanyl may each optionally be mono- or
disubstituted identically or differently by halogen,
(C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)haloalkyl, or R.sup.1 is
more preferably phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl,
pyrazolyl, triazolyl, thiazolyl, tetrazolyl, piperazinyl,
tetrahydrofuryl or oxetanyl, each of which is optionally mono- or
disubstituted identically or differently by halogen,
(C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)haloalkyl, R.sup.2a is
more preferably hydrogen, halogen, (C.sub.1-C.sub.4)alkyl
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulphinyl, (C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)haloalkylsulphinyl
or (C.sub.1-C.sub.4)haloalkylsulphonyl, R.sup.2b is more preferably
hydrogen or halogen, R.sup.3 is more preferably hydrogen,
(C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)haloalkylsulphinyl or
(C.sub.1-C.sub.4)haloalkylsulphonyl, R.sup.4 is more preferably
hydrogen, halogen, cyano or (C.sub.1-C.sub.3)alkyl, R.sup.5 is more
preferably (C.sub.1-C.sub.4)alkyl or
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl, n is more
preferably 0, 1 or 2, where, in the case that n=2, the meanings of
A.sup.3 may be the same or different. A.sup.1 is even more
preferably nitrogen or .dbd.C--R.sup.4, A.sup.2 is even more
preferably --N--R.sup.5 or oxygen, A.sup.3 is even more preferably
oxygen, A.sup.4 is even more preferably nitrogen or .dbd.C--H,
A.sup.5 is even more preferably nitrogen or .dbd.C--H, R.sup.1 is
even more preferably methyl, ethyl, n-propyl, i-propyl,
cyclopropyl, n-butyl, i-butyl, tert-butyl, cyclobutyl,
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
--(CH.sub.2).sub.2--S--C.sub.2H.sub.5,
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 or
##STR00003## R.sup.2a is even more preferably hydrogen,
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
trifluoromethylthio, trifluoromethylsulphonyl,
trifluoromethylsulphinyl, fluorine or chlorine, R.sup.2b is even
more preferably hydrogen, fluorine or chlorine, R.sup.3 is even
more preferably fluoromethyl, difluoromethyl, trifluoromethyl,
fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl,
pentafluoroethyl, trifluoromethylthio, trifluoromethylsulphonyl or
trifluoromethylsulphinyl, R.sup.4 is even more preferably hydrogen,
fluorine, chlorine, bromine or cyano, R.sup.5 is even more
preferably methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl,
n is even more preferably 0, 1 or 2. A.sup.1 is specifically
nitrogen (N) or .dbd.C--H, A.sup.2 is specifically --N--CH.sub.3 or
oxygen (O), A.sup.3 is specifically oxygen (O), A.sup.4 is
specifically nitrogen (N) or .dbd.C--H, A.sup.5 is specifically
.dbd.C--H, R.sup.1 is specifically methyl, ethyl, n-propyl,
i-propyl, trifluoromethyl, --(CH.sub.2).sub.2--S--C.sub.2H.sub.5,
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 or
##STR00004## R.sup.2a is specifically hydrogen, trifluoromethyl,
fluorine or chlorine, R.sup.2b is specifically hydrogen or
chlorine, R.sup.3 is specifically trifluoromethyl, n is
specifically 0, 1 or 2.
In a further preferred embodiment, the invention relates to
compounds of the formula (I-A)
##STR00005##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-B)
##STR00006##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-C)
##STR00007##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-D)
##STR00008##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-E)
##STR00009##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-F)
##STR00010##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-G)
##STR00011##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-H)
##STR00012##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-I)
##STR00013##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-J)
##STR00014##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-K)
##STR00015##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-L)
##STR00016##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-M)
##STR00017##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-N)
##STR00018##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-O)
##STR00019##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-P)
##STR00020##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-Q)
##STR00021##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-R)
##STR00022##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-S)
##STR00023##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-T)
##STR00024##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-U)
##STR00025##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-V)
##STR00026##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-W)
##STR00027##
In a further preferred embodiment, the invention relates to
compounds of the formula (I-X)
##STR00028##
In the formulae (I-A) to (I-X), the R.sup.1, R.sup.2a, R.sup.2b,
R.sup.3, A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and n radicals
are each as defined above.
In a further embodiment (Configuration 1), the invention relates to
compounds of the formula (I)
##STR00029## in which A.sup.1 is nitrogen, .dbd.N.sup.+--O.sup.- or
.dbd.C--R.sup.4, A.sup.2 is --N--R.sup.5, oxygen or sulphur,
A.sup.3 is oxygen, A.sup.4 is nitrogen, .dbd.N.sup.+--O.sup.- or
.dbd.C--R.sup.4, A.sup.5 is .dbd.C--H, R.sup.1 is
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, amino,
(C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino,
(C.sub.3-C.sub.8)cycloalkylamino,
(C.sub.1-C.sub.6)alkylcarbonylamino,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl-
,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6-
)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C-
.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonylamino,
aminosulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl-(C.sub.1-C.sub.6)alkyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl-(C.sub.1-C.sub.6)alkyl, or
is in each case identically or differently optionally mono- or
poly-aryl-, -hetaryl- or -heterocyclyl-substituted
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.3-C.sub.8)cycloalkyl, where aryl, hetaryl or heterocyclyl
may each independently be mono- or polysubstituted identically or
differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl,
carbamoyl, aminosulphonyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphonyl, (C.sub.1-C.sub.6)alkylsulphimino,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, (C.sub.1-C.sub.6)alky
lsulphoximino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.2-C.sub.6)alky lcarbonyl,
(C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.3-C.sub.6)trialkylsilyl or benzyl, or R.sup.1 is aryl,
hetaryl or heterocyclyl, each of which is optionally mono- or
polysubstituted identically or differently by halogen, cyano,
nitro, hydroxyl, amino, carboxyl, carbamoyl,
(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylsulphinyl, (C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphimino,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphimino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylsulphoximino,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphoximino-(C.sub.2-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.3-C.sub.6)trialkylsilyl, (.dbd.O) (only in the case of
heterocyclyl) or (.dbd.O).sub.2 (only in the case of heterocyclyl),
R.sup.2a, R.sup.2b, R.sup.3 and R.sup.4 are each independently
hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,
tri-(C.sub.1-C.sub.6)alkylsilyl, (C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl,
(C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylthiocarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl, (C.sub.1-C.sub.6)alky
lcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, NHCO--(C.sub.1-C.sub.6)alkyl
((C.sub.1-C.sub.6)alkylcarbonylamino), is aryl or hetaryl, each of
which is optionally mono- or polysubstituted identically or
differently, where (in the case of hetaryl) at least one carbonyl
group may optionally be present and/or where possible substituents
in each case are as follows: cyano, carboxyl, halogen, nitro,
acetyl, hydroxyl, amino, SCN, tri-(C.sub.1-C.sub.6)alkylsilyl,
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl, di(C.sub.1-C.sub.6)alky
laminosulphonyl, (C.sub.1-C.sub.6)alkylsulphoximino,
aminothiocarbonyl, (C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, R.sup.5 is
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyloxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl,
halo(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl-
,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6-
)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C-
.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
aminocarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylamino-(C.sub.1-C.sub.6)alkyl,
di(C.sub.1-C.sub.6)alkylamino-(C.sub.1-C.sub.6)alkyl or
(C.sub.3-C.sub.8)cycloalkylamino-(C.sub.1-C.sub.6)alkyl, n is 0, 1
or 2.
Preference (Configuration 2) is given to compounds of the formula
(I) in which A.sup.1 is nitrogen, .dbd.N.sup.+--O.sup.- or
.dbd.C--R.sup.4, A.sup.2 is --N--R.sup.5, oxygen or sulphur,
A.sup.3 is oxygen, A.sup.4 is nitrogen, .dbd.N.sup.+--O.sup.- or
.dbd.C--R.sup.4, A.sup.5 is .dbd.C--H, R.sup.1 is
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)cyanoalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl,
(C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)alkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.6)cycloalkylamino,
(C.sub.1-C.sub.4)alkylcarbonylamino,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylcarbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, or is (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkynyl, (C.sub.3-C.sub.6)cycloalkyl, each of
which is optionally mono- or disubstituted identically or
differently by aryl, hetaryl or heterocyclyl, where aryl, hetaryl
and heterocyclyl may each optionally be mono- or disubstituted
identically or differently by halogen, cyano, carbamoyl,
aminosulphonyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.4)cycloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)alkylsulphimino,
or R.sup.1 is aryl, hetaryl or heterocyclyl, each of which is
optionally mono- or disubstituted identically or differently by
halogen, cyano, carbamoyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)-alkoxy,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)alkylsulphimino,
(C.sub.1-C.sub.4)alkylsulphoximino, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.3-C.sub.4)trialkylsilyl, (.dbd.O) (only in the case of
heterocyclyl) or (.dbd.O).sub.2 (only in the case of heterocyclyl),
R.sup.2a, R.sup.2b, R.sup.3 and R.sup.4 are each independently
hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,
tri-(C.sub.1-C.sub.4)alkylsilyl, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)cyanoalkyl,
(C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)cyanoalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
aminothiocarbonyl, (C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di(C.sub.1-C.sub.4)alkylaminosulphonyl, aminothiocarbonyl,
NHCO--(C.sub.1-C.sub.4)alkyl ((C.sub.1-C.sub.4)alkylcarbonylamino),
is phenyl or hetaryl, each of which is mono- or disubstituted
identically or differently, where (in the case of hetaryl) at least
one carbonyl group may optionally be present and/or where possible
substituents in each case are as follows: cyano, halogen, nitro,
acetyl, amino, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)cyanoalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di(C.sub.1-C.sub.4)alkylaminosulphonyl, R.sup.5 is
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl,
(C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)alkynyloxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl-(C.sub.3-C.sub.6)cycloalkyl,
halo(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl-
, (C.sub.1-C.sub.4)alkylcarbonyl-(C.sub.1-C.sub.4)alkyl, n is 0, 1
or 2.
Particular preference (Configuration 3) is given to compounds of
the formula (I) in which A.sup.1 is nitrogen or .dbd.C--R.sup.4,
A.sup.2 is --N--R.sup.5 or oxygen, A.sup.3 is oxygen, A.sup.4 is
nitrogen or .dbd.C--R.sup.4, A.sup.5 is .dbd.C--H, R.sup.1 is
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl, or is
(C.sub.1-C.sub.4)alkyl optionally monosubstituted by phenyl,
pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl,
thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl,
where phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl,
pyrazolyl, triazolyl, thiazolyl, tetrazolyl, piperazinyl,
tetrahydrofuryl or oxetanyl may each optionally be mono- or
disubstituted identically or differently by halogen,
(C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)haloalkyl, or R.sup.1 is
phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl,
triazolyl, thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl or
oxetanyl, each of which is optionally mono- or disubstituted
identically or differently by halogen, (C.sub.1-C.sub.4)alkyl or
(C.sub.1-C.sub.4)haloalkyl, R.sup.2a is hydrogen, cyano,
aminocarbonyl, halogen, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)haloalkylsulphinyl or
(C.sub.1-C.sub.4)haloalkylsulphonyl, R.sup.2b is hydrogen,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkyl,
NHCO--(C.sub.1-C.sub.4)alkyl or halogen, R.sup.3 is hydrogen,
halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulphinyl, (C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl, or is phenyl, pyrazolyl or
imidazolyl, each of which is optionally monosubstituted by
trifluoromethyl, R.sup.4 is hydrogen, halogen, cyano or
(C.sub.1-C.sub.3)alkyl, R.sup.5 is (C.sub.1-C.sub.4)alkyl or
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl, n is 0, 1 or 2.
Very particular preference (Configuration 4) is given to compounds
of the formula (I) in which A.sup.1 is nitrogen or .dbd.C--R.sup.4,
A.sup.2 is --N--R.sup.5 or oxygen, A.sup.3 is oxygen, A.sup.4 is
nitrogen or .dbd.C--H, A.sup.5 is .dbd.C--H, R.sup.1 is methyl,
ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl,
tert-butyl, cyclobutyl, hydroxyethyl (--CH.sub.2--CH.sub.2--OH),
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
--(CH.sub.2).sub.2--S--C.sub.2H.sub.5,
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 or
##STR00030## R.sup.2a is hydrogen, cyano, aminocarbonyl
(CONH.sub.2), fluoromethyl, difluoromethyl, trifluoromethyl,
fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl,
pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,
dichlorofluoromethoxy, trifluoromethylthio,
trifluoromethylsulphonyl, trifluoromethylsulphinyl, fluorine or
chlorine, R.sup.2b is hydrogen, methoxy, ethoxy, trifluoromethyl,
methylcarbonylamino (NHCO-methyl), fluorine or chlorine, R.sup.3 is
fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl,
fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl,
pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,
dichlorofluoromethoxy, trifluoromethylthio,
trifluoromethylsulphonyl, trifluoromethylsulphinyl, or is phenyl,
pyrazol-1-yl or imidazol-1-yl, each of which is optionally
monosubstituted by trifluoromethyl, R.sup.4 is hydrogen, fluorine,
chlorine, bromine or cyano, R.sup.5 is methyl, ethyl, i-propyl,
methoxymethyl or methoxyethyl, n is 0, 1 or 2.
Emphasis (Configuration 5) is given to compounds of the formula (I)
in which A.sup.1 is nitrogen (N) or .dbd.C--H, A.sup.2 is
--N--CH.sub.3 or oxygen (O), A.sup.3 is oxygen (O), A.sup.4 is
nitrogen (N) or .dbd.C--H, A.sup.5 is .dbd.C--H, R.sup.1 is methyl,
ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl,
tert-butyl, cyclobutyl, hydroxyethyl (--CH.sub.2--CH.sub.2--OH),
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
--(CH.sub.2).sub.2--S--C.sub.2H.sub.5,
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 or
##STR00031## (oxetan-3-yl), R.sup.2a is hydrogen, cyano,
aminocarbonyl (CONH.sub.2), fluoromethyl, difluoromethyl,
trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,
tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,
trifluoromethylthio, trifluoromethylsulphonyl,
trifluoromethylsulphinyl, fluorine or chlorine, R.sup.2b is
hydrogen, methoxy, ethoxy, trifluoromethyl, methylcarbonylamino
(NHCO-methyl), fluorine or chlorine, R.sup.3 is fluorine, chlorine,
fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,
difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,
trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphonyl,
trifluoromethylsulphinyl, or is phenyl,
##STR00032## (pyrazol-1-yl) or
##STR00033## (imidazol-1-yl), each of which is optionally
monosubstituted by trifluoromethyl, n is 0, 1 or 2.
Particular emphasis (Configuration 6) is given to compounds of the
formula (I) in which A.sup.1 is nitrogen (N) or .dbd.C--H, A.sup.2
is --N--CH.sub.3 or oxygen (O), A.sup.3 is oxygen (O), A.sup.4 is
nitrogen (N) or .dbd.C--H, A.sup.5 is .dbd.C--H, R.sup.1 is methyl,
ethyl, n-propyl, i-propyl, trifluoromethyl,
--CH.sub.2--CH.sub.2--F, --CH.sub.2--CH.sub.2--OH,
--(CH.sub.2).sub.2--S--C.sub.2H.sub.5,
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 or
##STR00034## R.sup.2a is hydrogen, trifluoromethyl, cyano,
CONH.sub.2, fluorine or chlorine, R.sup.2b is hydrogen, chlorine,
trifluoromethyl, methoxy or NHCOCH.sub.3, R.sup.3 is
pentafluoroethyl, trifluoromethyl, chlorine,
4-CF.sub.3(C.sub.6H.sub.4), 4-(CF.sub.3)pyrazol-1-yl,
3-(CF.sub.3)pyrazol-1-yl or 4-(CF.sub.3)imidazol-1-yl, n is 0, 1 or
2.
In a further preferred embodiment, the invention relates to the
compounds of the formula (I) where R.sup.1, R.sup.2a, R.sup.3,
A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and n are each as
defined above, especially as defined in Configuration (1) or
Configuration (2) or Configuration (3) or Configuration (4) or
Configuration (5) or Configuration (6), and R.sup.2b is acetyl,
amino, SCN, tri-(C.sub.1-C.sub.6)alkylsilyl,
(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl,
(C.sub.1-C.sub.6)alkyl(C.sub.3-C.sub.8)cycloalkyl (where the bond
is via the cycloalkyl substituted by alkyl),
halo(C.sub.3-C.sub.8)cycloalkyl, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl,
(C.sub.2-C.sub.6)cyanoalkynyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)alkylthiocarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di-(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di-(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl,
di-(C.sub.1-C.sub.6)alkylaminosulphonyl,
(C.sub.1-C.sub.6)alkylsulphoximino, aminothiocarbonyl,
(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino, NHCO--(C.sub.1-C.sub.6)alkyl
((C.sub.1-C.sub.6)alkylcarbonylamino), is in each case optionally
singly or multiply, identically or differently substituted hetaryl,
where at least one carbonyl group may optionally be present and/or
where possible substituents in each case are as follows: cyano,
carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,
tri-(C.sub.1-C.sub.6)alkylsilyl, (C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl,
(C.sub.1-C.sub.6)hydroxyalkyl,
hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.1-C.sub.6)cyanoalkoxy,
(C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio,
(C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)haloalkylsulphinyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphinyl,
(C.sub.1-C.sub.6)alkylsulphinyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)haloalkylsulphonyl,
(C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulphonyl,
(C.sub.1-C.sub.6)alkylsulphonyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkylsulphonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl,
(C.sub.1-C.sub.6)haloalkylcarbonyl,
(C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl,
(C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl,
(C.sub.1-C.sub.6)alkylaminocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.2-C.sub.6)alkenylaminocarbonyl,
di-(C.sub.2-C.sub.6)-alkenylaminocarbonyl,
(C.sub.3-C.sub.8)cycloalkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulphonylamino, (C.sub.1-C.sub.6)alkylamino,
di-(C.sub.1-C.sub.6)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.6)alkylaminosulphonyl, di-(C.sub.1-C.sub.6)alky
laminosulphonyl, (C.sub.1-C.sub.6)alkylsulphoximino,
aminothiocarbonyl, (C.sub.1-C.sub.6)alkylaminothiocarbonyl,
di-(C.sub.1-C.sub.6)alkylaminothiocarbonyl,
(C.sub.3-C.sub.8)cycloalkylamino.
In a further preferred embodiment, the invention relates to the
compounds of the formula (I) where R.sup.1, R.sup.2a, R.sup.3,
A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and n are each as
defined above, especially as defined in Configuration (1) or
Configuration (2) or Configuration (3) or Configuration (4) or
Configuration (5) or Configuration (6), and R.sup.2b is acetyl,
amino, SCN, tri-(C.sub.1-C.sub.4)alkylsilyl,
(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.6)cycloalkyl,
(C.sub.1-C.sub.4)alkyl(C.sub.3-C.sub.6)cycloalkyl (where the bond
is via the cycloalkyl substituted by alkyl),
halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl,
(C.sub.2-C.sub.4)alkynyl, (C.sub.2-C.sub.4)haloalkynyl,
(C.sub.2-C.sub.4)cyanoalkynyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
(C.sub.1-C.sub.4)alkylaminocarbonyl,
di-(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di-(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di-(C.sub.1-C.sub.4)alkylaminosulphonyl, aminothiocarbonyl,
NHCO--(C.sub.1-C.sub.4)alkyl ((C.sub.1-C.sub.4)alkylcarbonylamino),
is in each case singly or doubly, identically or differently
substituted hetaryl, where at least one carbonyl group may
optionally be present and/or where possible substituents in each
case are as follows: cyano, halogen, nitro, acetyl, amino,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)hydroxyalkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl,
(C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)cyanoalkoxy,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylhydroxyimino, (C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)haloalkyl-(C.sub.1-C.sub.4)alkoxyimino,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylthio-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphinyl,
(C.sub.1-C.sub.4)haloalkylsulphinyl,
(C.sub.1-C.sub.4)alkylsulphinyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyl,
(C.sub.1-C.sub.4)haloalkylsulphonyl,
(C.sub.1-C.sub.4)alkylsulphonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylsulphonyloxy, (C.sub.1-C.sub.4)alkylcarbonyl,
(C.sub.1-C.sub.4)haloalkylcarbonyl, aminocarbonyl,
(C.sub.1-C.sub.4)alkylaminocarbonyl,
di-(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulphonylamino, (C.sub.1-C.sub.4)alkylamino,
di-(C.sub.1-C.sub.4)alkylamino, aminosulphonyl,
(C.sub.1-C.sub.4)alkylaminosulphonyl,
di-(C.sub.1-C.sub.4)alkylaminosulphonyl.
In a further preferred embodiment, the invention relates to the
compounds of the formula (I) where R.sup.1, R.sup.2a, R.sup.3,
A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and n are each as
defined above, especially as defined in Configuration (1) or
Configuration (2) or Configuration (3) or Configuration (4) or
Configuration (5) or Configuration (6), and R.sup.2b is
(C.sub.1-C.sub.4)alkoxy or NHCO--(C.sub.1-C.sub.4)alkyl.
In a further preferred embodiment, the invention relates to the
compounds of the formula (I) where R.sup.1, R.sup.2a, R.sup.3,
A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and n are each as
defined above, especially as defined in Configuration (1) or
Configuration (2) or Configuration (3) or Configuration (4) or
Configuration (5) or Configuration (6), and R.sup.2b is methoxy,
ethoxy or NHCO-methyl.
In a further preferred embodiment, the invention relates to the
compounds of the formula (I) where R.sup.1, R.sup.2a, R.sup.3,
A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and n are each as
defined above, especially as defined in Configuration (1) or
Configuration (2) or Configuration (3) or Configuration (4) or
Configuration (5) or Configuration (6), and R.sup.2b is methoxy or
NHCO-methyl.
R.sup.2b is joined in the 3 or 5 position:
##STR00035##
In the preferred definitions, unless stated otherwise,
halogen is selected from the group of fluorine, chlorine, bromine
and iodine, preferably in turn from the group of fluorine, chlorine
and bromine,
aryl (including as part of a larger unit, for example arylalkyl) is
selected from the group of phenyl, naphthyl, anthryl,
phenanthrenyl, and is preferably in turn phenyl,
hetaryl (synonymous with heteroaryl, including as part of a larger
unit, for example hetarylalkyl) is selected from the group of
furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl,
oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl,
1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl,
1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl,
1,2,5-thiadiazolyl, tetrazolyl, pyridyl, pyrimidyl, pyridazinyl,
pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl,
benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl,
isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl,
benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole,
quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl,
quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl
and indolizinyl,
heterocyclyl is a saturated 4-, 5- or 6-membered ring containing 1
or 2 nitrogen atoms and/or one oxygen atom and/or one sulphur atom,
for example azetidinyl, pyrrolidinyl, piperidinyl, oxetanyl,
tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, thietanyl,
tetrahydrothiophenyl, tetrahydrothiopyranyl, piperazinyl,
morpholinyl and thiomorpholinyl.
In the particularly preferred definitions, unless stated
otherwise,
halogen is selected from the group of fluorine, chlorine, bromine
and iodine, preferably in turn from the group of fluorine, chlorine
and bromine,
aryl (including as part of a larger unit, for example arylalkyl) is
selected from the group of phenyl, naphthyl, anthryl,
phenanthrenyl, and is preferably in turn phenyl,
hetaryl (including as part of a larger unit, for example
hetarylalkyl) is selected from the group of pyridyl, pyrimidyl,
pyrazinyl, pyridazinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl
and tetrazolyl,
heterocyclyl is selected from the group of oxetanyl,
tetrahydrofuryl and piperazinyl.
In the context of the present invention, unless defined differently
elsewhere, the term "alkyl", either on its own or else in
combination with further terms, for example haloalkyl, is
understood to mean a radical of a saturated aliphatic hydrocarbon
group which has 1 to 12 carbon atoms and may be branched or
unbranched. Examples of C.sub.1-C.sub.12-alkyl radicals are methyl,
ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,
tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,
1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl,
hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and
n-dodecyl. From among these alkyl radicals, particular preference
is given to C.sub.1-C.sub.6-alkyl radicals. Special preference is
given to C.sub.1-C.sub.4-alkyl radicals.
According to the invention, unless defined differently elsewhere,
the term "alkenyl", either on its own or else in combination with
further terms, is understood to mean a straight-chain or branched
C.sub.2-C.sub.12-alkenyl radical which has at least one double
bond, for example vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl,
2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl,
3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl, 2-hexenyl,
3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl. Among these,
preference is given to C.sub.2-C.sub.6-alkenyl radicals and
particular preference to C.sub.2-C.sub.4-alkenyl radicals.
According to the invention, unless defined differently elsewhere,
the term "alkynyl", either on its own or else in combination with
further terms, is understood to mean a straight-chain or branched
C.sub.2-C.sub.12-alkynyl radical which has at least one triple
bond, for example ethynyl, 1-propynyl and propargyl. Among these,
preference is given to C.sub.3-C.sub.6-alkynyl radicals and
particular preference to C.sub.3-C.sub.4-alkynyl radicals. The
alkynyl radical may also contain at least one double bond.
According to the invention, unless defined differently elsewhere,
the term "cycloalkyl", either on its own or else in combination
with further terms, is understood to mean a
C.sub.3-C.sub.8-cycloalkyl radical, for example cyclopropyl,
cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
Among these, preference is given to C.sub.3-C.sub.6-cycloalkyl
radicals.
The term "alkoxy", either on its own or else in combination with
further terms, for example haloalkoxy, is understood to mean an
O-alkyl radical, where the term "alkyl" is as defined above.
Halogen-substituted radicals, for example haloalkyl, are mono- or
polyhalogenated, up to the maximum number of possible substituents.
In the case of polyhalogenation, the halogen atoms can be identical
or different. In this case, halogen is fluorine, chlorine, bromine
or iodine, especially fluorine, chlorine or bromine.
Unless stated otherwise, optionally substituted radicals may be
mono- or polysubstituted, where the substituents in the case of
polysubstitution may be the same or different.
The radical definitions or elucidations given above in general
terms or within areas of preference apply to the end products and
correspondingly to the starting materials and intermediates. These
radical definitions can be combined with one another as desired,
i.e. including combinations between the respective preferred
ranges.
Preference is given in accordance with the invention to using
compounds of the formula (I) where a combination of the definitions
listed above as preferred is present.
Particular preference is given in accordance with the invention to
using compounds of the formula (I) where a combination of the
definitions listed above as particularly preferred is present.
Very particular preference is given in accordance with the
invention to using compounds of the formula (I) where a combination
of the definitions listed above as very particularly preferred is
present.
Emphasis is given in accordance with the invention to using
compounds of the formula (I) where a combination of the definitions
listed above as specific is present.
Particular emphasis is given in accordance with the invention to
using compounds of the formula (I) where a combination of the
definitions listed above as very specific is present.
Depending on the nature of the substituents, the compounds of the
formula (I) may be in the form of geometric and/or optically active
isomers or corresponding isomer mixtures in different compositions.
These stereoisomers are, for example, enantiomers, diastereomers,
atropisomers or geometric isomers. The invention thus encompasses
pure stereoisomers and any desired mixtures of these isomers.
The inventive compounds of the formula (I) can be obtained by the
processes shown in the following schemes:
Process A
##STR00036##
The R.sup.1, R.sup.2a, R.sup.2b, R.sup.3, A.sup.1, A.sup.2,
A.sup.3, A.sup.4, A.sup.5 and n radicals are each as defined
above.
Step a)
The compounds of the formula (IV) can be prepared in analogy to the
process described in U.S. Pat. No. 5,576,335 by the reaction of
compounds of the formula (II) with carboxylic acids of the formula
(III) in the presence of a condensing agent.
Compounds of the formula (II) are either commercially available or
can be prepared by known methods, for example analogously to the
processes described in US2003/69257 or WO2006/65703.
Carboxylic acids of the formula (III) are either commercially
available or can be prepared by known methods, for example
analogously to the processes described in US2010/234604,
WO2012/61926 or Bioorganic and Medicinal Chemistry Letters, 18
(2008), 5023-5026.
The reaction of the compounds of the formula (II) with carboxylic
acids of the formula (III) can be effected neat or in a solvent,
preference being given to conducting the reaction in a solvent
selected from customary solvents that are inert under the
prevailing reaction conditions. Preference is given to ethers, for
example diisopropyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane; halogenated hydrocarbons, for example
dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane or chlorobenzene; nitriles, for example
acetonitrile or propionitrile; aromatic hydrocarbons, for example
toluene or xylene; aprotic polar solvents, for example
N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen
compounds, for example pyridine.
Suitable condensing agents are, for example, carbodiimides such as
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI)
or 1,3-dicyclohexylcarbodiimide.
The reaction can be effected under reduced pressure, at standard
pressure or under elevated pressure and at temperatures of 0 to
180.degree. C., preference being given to effecting the reaction at
standard pressure and temperatures of 20 to 140.degree. C.
Step b)
The compounds of the formula (I) can be prepared by condensing the
compounds of the formula (IV), for example analogously to the
processes described in WO2012/86848.
The conversion to compounds of the formula (I) can be effected neat
or in a solvent, preference being given to conducting the reaction
in a solvent selected from the customary solvents that are inert
under the prevailing reaction conditions. Preference is given to
ethers, for example diisopropyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane, tert-butyl methyl ether; halogenated
hydrocarbons, for example dichloromethane, chloroform, carbon
tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, for
example acetonitrile or propionitrile; aromatic hydrocarbons, for
example toluene or xylene; aprotic polar solvents, for example
N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen
compounds, for example pyridine.
The reaction can be conducted in the presence of a condensing
agent, an acid, a base or a chlorinating agent.
Examples of suitable condensing agents are carbodiimides such as
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI)
or 1,3-dicyclohexylcarbodiimide; anhydrides such as acetic
anhydride, trifluoroacetic anhydride; a mixture of
triphenylphosphine, a base and carbon tetrachloride, or a mixture
of triphenylphosphine and azo diester, for example
diethylazodicarboxylic acid.
Examples of suitable acids which can be used in the reaction
described are sulphonic acids such as para-toluenesulphonic acid;
carboxylic acids such as acetic acid, or polyphosphoric acids.
Examples of suitable bases are nitrogen heterocycles such as
pyridine, picoline, 2,6-lutidine,
1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as
triethylamine and N,N-diisopropylethylamine; inorganic bases such
as potassium phosphate, potassium carbonate and sodium hydride.
An example of a suitable chlorinating agent is phosphorus
oxychloride.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
0.degree. C. to 200.degree. C.
Process B
##STR00037##
The R.sup.1, R.sup.2a, R.sup.2b, R.sup.3, A.sup.1, A.sup.2, A,
A.sup.4, A.sup.5 and n radicals are each as defined above.
Step a)
In a further embodiment of the invention, compounds of the formula
(IV) can be prepared by the reaction of compounds of the formula
(II) with carbonyl chlorides of the formula (V) in the presence of
a condensing agent.
Carbonyl chlorides of the formula (V) are either commercially
available or can be prepared by known methods, for example
analogously to the processes described in US2010/234603 or
US2010/234604.
The reaction of the compounds of the formula (II) with carbonyl
chlorides of the formula (V) can be effected neat or in a solvent,
preference being given to conducting the reaction in a solvent
selected from customary solvents that are inert under the
prevailing reaction conditions. Preference is given to ethers, for
example diisopropyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane; halogenated hydrocarbons, for example
dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane or chlorobenzene; aliphatic hydrocarbons such as
hexane, heptane or octane; aromatic hydrocarbons, for example
toluene or xylene; nitriles, for example acetonitrile or
propionitrile; aprotic polar solvents, for example
N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen
compounds, for example pyridine.
The reaction is preferably effected in the presence of a base.
Suitable bases of the inorganic bases which are typically used in
such reactions. Preference is given to using bases selected by way
of example from the group consisting of acetates, phosphates,
carbonyl cates and hydrogencarbonates of alkali metals or
alcustomaline earth metals. Particular preference is given to
sodium acetate, sodium phosphate, potassium alkaline earth metals.
Particular preference is given to sodium acetate, sodium phosphate,
potassium phosphate, caesium carbonate, sodium carbonate, potassium
carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate.
Further suitable bases are tertiary amines such as triethylamine
and N,N-diisopropylethylamine, and nitrogen heterocycles such as
pyridine, picoline, 2,6-lutidine, 4-dimethylaminopyridine and
1,8-diazabicyclo[5.4.0]-7-undecene (DBU).
The reaction can be effected under reduced pressure, at standard
pressure or under elevated pressure and at temperatures of
-20.degree. C. to 100.degree. C., preference being given to
effecting the reaction at standard pressure and temperatures of
0.degree. C. to 80.degree. C.
Step b)
The further conversion of the compounds of the formula (IV) to
compounds of the formula (I) is effected as in process A, step
b).
Process C
##STR00038##
The R.sup.1, R.sup.2a, R.sup.2b, R.sup.3, A.sup.1, A.sup.2,
A.sup.3, A.sup.4, A.sup.5 and n radicals are each as defined
above.
In a further embodiment of the invention, compounds of the formula
(I) can be prepared in a one-stage process from the intermediate
compounds of the formulae (II) and (III) in the presence of a
condensing agent.
The conversion to compounds of the formula (I) can be effected neat
or in a solvent, preference being given to conducting the reaction
in a solvent selected from the customary solvents that are inert
under the prevailing reaction conditions. Preference is given to
ethers, for example diisopropyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane, tert-butyl methyl ether; halogenated
hydrocarbons, for example dichloromethane, chloroform, carbon
tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such
as methanol, ethanol or isopropanol; nitriles, for example
acetonitrile or propionitrile; aromatic hydrocarbons, for example
toluene or xylene; aprotic polar solvents, for example
N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen
compounds, for example pyridine.
Examples of suitable condensing agents are carbodiimides such as
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI)
or 1,3-dicyclohexylcarbodiimide; anhydrides such as acetic
anhydride, trifluoroacetic anhydride; a mixture of
triphenylphosphine, a base and carbon tetrachloride, or a mixture
of triphenylphosphine and an azo diester, for example
diethylazodicarboxylic acid.
The reaction can be conducted in the presence of an acid or a
base.
Examples of an acid which can be used in the reaction described are
sulphonic acids such as methanesulphonic acid or
para-toluenesulphonic acid; carboxylic acids such as acetic acid,
or polyphosphoric acids.
Examples of suitable bases are nitrogen heterocycles such as
pyridine, picoline, 2,6-lutidine,
1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as
triethylamine and N,N-diisopropylethylamine; inorganic bases such
as potassium phosphate, potassium carbonate and sodium hydride.
The reaction can be conducted in the presence of a suitable
catalyst, for example 1-hydroxybenzotriazole.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
0.degree. C. to 200.degree. C.
Process D
##STR00039##
The R.sup.1, R.sup.2a, R.sup.2b, R.sup.3, A.sup.1, A.sup.2,
A.sup.3, A.sup.4, A.sup.5 and n radicals are each as defined
above.
In a further embodiment of the invention, compounds of the formula
(I) can be prepared in a one-stage process from the intermediate
compounds of the formulae (II) and (V).
The conversion to compounds of the formula (I) can be effected neat
or in a solvent, preference being given to conducting the reaction
in a solvent selected from the customary solvents that are inert
under the prevailing reaction conditions. Preference is given to
ethers, for example diisopropyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane, tert-butyl methyl ether; halogenated
hydrocarbons, for example dichloromethane, chloroform, carbon
tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such
as methanol, ethanol or isopropanol; nitriles, for example
acetonitrile or propionitrile; aromatic hydrocarbons, for example
toluene or xylene; aprotic polar solvents, for example
N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen
compounds, for example pyridine.
The reaction is preferably effected in the presence of a base.
Suitable bases are inorganic bases which are typically used in such
reactions. Preference is given to using bases selected by way of
example from the group consisting of acetates, phosphates,
hydroxides, carbonates and hydrogencarbonates of alkali metals or
alkaline earth metals. Preference is given to caesium carbonate,
sodium carbonate, potassium carbonate, sodium hydroxide and
potassium hydroxide. Further suitable bases are tertiary amines
such as triethylamine and N,N-diisopropylethylamine, nitrogen
heterocycles such as pyridine, picoline, 2,6-lutidine,
4-dimethylaminopyridine and 1,8-diazabicyclo[5.4.0]-7-undecene
(DBU).
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
0.degree. C. to 200.degree. C.
Process E
##STR00040##
The R.sup.1, R.sup.2a, R.sup.2b, R.sup.3, A.sup.1, A.sup.2,
A.sup.3, A.sup.4, A.sup.5 and n radicals are each as defined
above.
In a further embodiment of the invention, compounds of the formula
(I) can be prepared from the compounds of the formula (II) and the
aldehydes of the formula (VI) in the presence of an oxidizing
agent.
Aldehydes of the formula (VI) are either commercially available or
can be prepared by known methods, for example analogously to the
processes described in US2009/192195, US2010/227894 or Angewandte
Chemie, International Edition, 48 (2009), 7064-7068.
The conversion to compounds of the formula (I) can be effected neat
or in a solvent, preference being given to conducting the reaction
in a solvent. Preference is given to ethers, for example
diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,
tert-butyl methyl ether; halogenated hydrocarbons, for example
dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane or chlorobenzene; alcohols such as methanol,
ethanol or isopropanol; esters such as ethyl acetate; nitriles, for
example acetonitrile or propionitrile; aromatic hydrocarbons, for
example toluene or xylene; aprotic polar solvents, for example
N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen
compounds, for example pyridine.
The reaction can be conducted in the presence of an acid. Examples
of acids which can be used in the reaction described are sulphonic
acids such as methanesulphonic acid or para-toluenesulphonic acid;
carboxylic acids such as acetic acid, or polyphosphoric acids.
The reaction can also be conducted in the presence of a sulphite.
Examples of sulphites which can be used in the reaction described
are sodium hydrogensulphite or sodium sulphite.
Examples of oxidizing agents which find use in the reaction
described are oxygen, copper(II) chloride or DDQ.
The reaction can be effected under reduced pressure, at standard
pressure or under elevated pressure and at temperatures of 0 to
200.degree. C., preference being given to effecting the reaction at
standard pressure and temperatures of 20 to 150.degree. C.
Process F
##STR00041##
The R.sup.1, R.sup.2a, R.sup.2b, R.sup.3, A.sup.1, A.sup.2,
A.sup.3, A.sup.4, A.sup.5 and n radicals are each as defined above,
and X.sup.1 is halogen.
Step a)
The compounds of the formula (VIII) can be prepared in analogy to
the process described in U.S. Pat. No. 5,576,335 by the reaction of
compounds of the formula (II) with a carboxylic acid of the formula
(VIIa) or with a carbonyl chloride of the formula (VIIb) in the
presence of a condensing agent or a base.
Compounds of the formula (II) are either commercially available or
can be prepared by known methods, for example analogously to the
processes described in US2003/69257 or WO2006/65703.
Carboxylic acids of the formula (VIIa) are either commercially
available or can be prepared by known methods, for example
analogously to the processes described in US2010/234604,
WO2012/61926 or Bioorganic and Medicinal Chemistry Letters, 18
(2008), 5023-5026.
Carbonyl chlorides of the formula (VIIb) are either commercially
available or can be prepared by known methods, for example
analogously to the processes described in US2010/234603 or
US2010/234604.
The reaction of the compounds of the formula (II) with carboxylic
acids of the formula (VIIa) or carbonyl chlorides of the formula
(VIIb) can be effected neat or in a solvent, preference being given
to conducting the reaction in a solvent selected from customary
solvents that are inert under the prevailing reaction conditions.
Preference is given to ethers, for example diisopropyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated
hydrocarbons, for example dichloromethane, chloroform, carbon
tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, for
example acetonitrile or propionitrile; aromatic hydrocarbons, for
example toluene or xylene; aprotic polar solvents, for example
N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen
compounds, for example pyridine.
Suitable condensing agents are, for example, carbodiimides such as
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI)
or 1,3-dicyclohexylcarbodiimide.
Suitable bases are inorganic bases which are typically used in such
reactions. Preference is given to using bases selected by way of
example from the group consisting of acetates, phosphates,
carbonates and hydrogencarbonates of alkali metals or alkaline
earth metals. Particular preference is given to sodium acetate,
sodium phosphate, potassium phosphate, caesium carbonate, sodium
carbonate, potassium carbonate, sodium hydrogencarbonate, potassium
hydrogencarbonate.
The reaction can be effected under reduced pressure, at standard
pressure or under elevated pressure and at temperatures of 0 to
180.degree. C., preference being given to effecting the reaction at
standard pressure and temperatures of 20 to 140.degree. C.
Step b)
The compounds of the formula (IX) can be prepared by condensing the
intermediate compounds of the formula (VIII), for example
analogously to the processes described in WO2012/86848.
The conversion to compounds of the formula (IX) can be effected
neat or in a solvent, preference being given to conducting the
reaction in a solvent selected from customary solvents that are
inert under the prevailing reaction conditions. Preference is given
to ethers, for example diisopropyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane, tert-butyl methyl ether; halogenated
hydrocarbons, for example dichloromethane, chloroform, carbon
tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, for
example acetonitrile or propionitrile; aromatic hydrocarbons, for
example toluene or xylene; aprotic polar solvents, for example
N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen
compounds, for example pyridine.
The reaction can be conducted in the presence of a condensing
agent, an acid, a base or a chlorinating agent.
Examples of suitable condensing agents are carbodiimides such as
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI)
or 1,3-dicyclohexylcarbodiimide; anhydrides such as acetic
anhydride, trifluoroacetic anhydride; a mixture of
triphenylphosphine, a base and carbon tetrachloride, or a mixture
of triphenylphosphine and an azo diester, for example
diethylazodicarboxylic acid.
Examples of suitable acids which can be used in the reaction
described are sulphonic acids such as para-toluenesulphonic acid;
carboxylic acids such as acetic acid, or polyphosphoric acids.
Examples of suitable bases are nitrogen heterocycles such as
pyridine, picoline, 2,6-lutidine,
1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as
triethylamine and N,N-diisopropylethylamine; inorganic bases such
as potassium phosphate, potassium carbonate and sodium hydride.
An example of a suitable chlorinating agent is phosphorus
oxychloride.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
0.degree. C. to 200.degree. C.
Step c)
The compounds of the formula (I) where n is 0 can be prepared by
reacting the intermediate compounds of the formula (IX) with the
intermediate compounds of the formula (X) in the presence of a
base.
Mercaptan derivatives of the formula (X), for example methyl
mercaptan, ethyl mercaptan or isopropyl mercaptan, are either
commercially available or can be prepared by known methods, for
example analogously to the processes described in US2006/25633,
US2006/111591, U.S. Pat. No. 2,820,062, Chemical Communications, 13
(2000), 1163-1164 or Journal of the American Chemical Society, 44
(1922), p. 1329.
The conversion to compounds of the formula (I) where n is 0 can be
effected neat or in a solvent, preference being given to conducting
the reaction in a solvent selected from the customary solvents that
are inert under the prevailing reaction conditions. Preference is
given to ethers, for example diisopropyl ether, dioxane,
tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether;
nitriles, for example acetonitrile or propionitrile; aromatic
hydrocarbons, for example toluene or xylene; aprotic polar
solvents, for example N,N-dimethylformamide, N-methylpyrrolidone or
dimethyl sulphoxide.
Examples of suitable bases are inorganic bases from the group
consisting of acetates, phosphates and carbonates of alkali metals
or alkaline earth metals. Preference is given to caesium carbonate,
sodium carbonate and potassium carbonate. Further suitable bases
are alkali metal hydrides, for example sodium hydride.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
0.degree. C. to 200.degree. C.
In the reaction described, X.sup.1 is preferably a fluorine or
chlorine atom.
Step d)
The compounds of the formula (I) where A.sup.3 is oxygen and n is 1
can be prepared by oxidizing the compounds of the formula (I) where
n is 0. The oxidation is generally conducted in a solvent selected
from customary solvents which are inert under the prevailing
reaction conditions. Preference is given to halogenated
hydrocarbons, for example dichloromethane, chloroform, carbon
tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such
as methanol or ethanol; formic acid, acetic acid, propionic acid or
water.
Examples of suitable oxidizing agents are hydrogen peroxide,
meta-chloroperbenzoic acid or sodium periodate.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
-20.degree. C. to 120.degree. C.
Step e)
The compounds of the formula (I) where A.sup.3 is oxygen and n is 2
can be prepared by oxidizing the compounds of the formula (I) where
A.sup.3 is oxygen and n is 1. The oxidation is generally conducted
in a solvent. Preference is given to halogenated hydrocarbons, for
example dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane or chlorobenzene; alcohols such as methanol or
ethanol; formic acid, acetic acid, propionic acid or water.
Examples of suitable oxidizing agents are hydrogen peroxide and
meta-chloroperbenzoic acid.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
-20.degree. C. to 120.degree. C.
Step f)
The compounds of the formula (I) where A.sup.3 is oxygen and n is 2
can also be prepared in a one-stage process by oxidizing the
compounds of the formula (I) where n is 0. The oxidation is
generally conducted in a solvent. Preference is given to
halogenated hydrocarbons, for example dichloromethane, chloroform,
carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols
such as methanol or ethanol; formic acid, acetic acid, propionic
acid or water.
Examples of suitable oxidizing agents are hydrogen peroxide and
meta-chloroperbenzoic acid.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
-20.degree. C. to 120.degree. C.
Process G
Compounds of the formula (I) for which R.sup.3=halogen can be
converted to other compounds of the formula (I) for which R.sup.3
is another radical according to the definition.
Compounds of the formula (I) for which R.sup.3 is a C-bonded
radical from the group of aryl or heteroaryl according to the
definition can be prepared, for example, from compounds of the
formula (I) for which R.sup.3 is preferably halogen from the group
of chlorine or bromine by commonly known methods (cf. Chem. Rev.
1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695;
Metal-Catalyzed Cross-Coupling Reactions (eds.: A. de Meijere, F.
Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004).
For example, compounds in which R.sup.3 is preferably chlorine or
bromine can be reacted with suitable arylboronic acids or esters
thereof by known methods (cf. WO2010071819) in the presence of
suitable catalysts from the group of the transition metal salts to
give compounds of the formula (I) in which R.sup.3 is a radical
from the group of aryl. Examples of preferred coupling catalysts
include palladium catalysts such as
[1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) or
tetrakis(triphenylphosphine)palladium. Suitable basic reaction
auxiliaries used to conduct the processes are preferably carbonates
of sodium or potassium.
Some of the (hetero)arylboronic acids or (hetero)arylboronic esters
required are known and/or commercially available, for example
prepared by commonly known methods (cf. Boronic Acids (eds.: D. G.
Hall), 2nd ed., Wiley-VCH, Weinheim, 2011).
The preparation of compounds of the formula (I) in which R.sup.3 is
an N-bonded hetaryl, for example imidazol-1-yl and pyrazol-1-yl can
be effected by methods known from the literature (see, for example,
Journal of Organic Chemistry (2010), 69, 5578), preferably in the
presence of copper(I) iodide and basic reaction auxiliaries, for
example trans-N,N'-dimethylcyclohexane-1,2-diamine and potassium
carbonate, in a suitable solvent or diluent. Useful solvents or
diluents include all inert organic solvents, for example aliphatic
or aromatic hydrocarbons. Preference is given to using toluene.
Some of the compounds of the formula (II) are novel.
Novel compounds are those of the formula (IIa)
##STR00042## in which R.sup.3 is as defined above, though R.sup.3
must not be chlorine, bromine or CHO.
The present invention also provides compounds of the formula (IIa)
in which R.sup.3 is (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)haloalkylsulphinyl or
(C.sub.1-C.sub.4)haloalkylsulphonyl, where R.sup.3 is not CF.sub.3
or CHF.sub.2.
Preferably, R.sup.3 is CH.sub.2F, C.sub.2H.sub.4F,
C.sub.2H.sub.3F.sub.2, C.sub.2H.sub.2F.sub.3, C.sub.2HF.sub.4,
C.sub.2F.sub.5, n-C.sub.3F.sub.7, i-C.sub.3F.sub.7, OCH.sub.2F,
SCH.sub.2F, SOCH.sub.2F, SO.sub.2CH.sub.2F, OCHF.sub.2, SCHF.sub.2,
SOCHF.sub.2, SO.sub.2CHF.sub.2, OCF.sub.3, OCF.sub.2Cl,
OCFCl.sub.2, SCF.sub.3, SOCF.sub.3, SO.sub.2CF.sub.3,
OC.sub.2H.sub.4F, SC.sub.2H.sub.4F, SOC.sub.2H.sub.4F,
SO.sub.2C.sub.2H.sub.4F, OC.sub.2H.sub.3F.sub.2,
SC.sub.2H.sub.3F.sub.2, SOC.sub.2H.sub.3F.sub.2,
SO.sub.2C.sub.2H.sub.3F.sub.2, OC.sub.2H.sub.2F.sub.3,
SC.sub.2H.sub.2F.sub.3, SOC.sub.2H.sub.2F.sub.3,
SO.sub.2C.sub.2H.sub.2F.sub.3, OC.sub.2HF.sub.4, SC.sub.2HF.sub.4,
SOC.sub.2HF.sub.4, SO.sub.2C.sub.2HF.sub.4, OC.sub.2F.sub.5,
SC.sub.2F.sub.5, SOC.sub.2F.sub.5, SO.sub.2C.sub.2F.sub.5,
n-OC.sub.3F.sub.7, n-SC.sub.3F.sub.7, n-SOC.sub.3F.sub.7,
n-SO.sub.2C.sub.3F.sub.7, i-OC.sub.3F.sub.7, i-SC.sub.3F.sub.7,
i-SOC.sub.3F.sub.7 or i-SO.sub.2C.sub.3F.sub.7.
More preferably, R.sup.3 is CH.sub.2F, OCF.sub.3, C.sub.2H.sub.4F,
C.sub.2H.sub.3F.sub.2, C.sub.2H.sub.2F.sub.3, C.sub.2HF.sub.4,
C.sub.2F.sub.5, SCF.sub.3, SOCF.sub.3 or SO.sub.2CF.sub.3.
Most preferably, R.sup.3 is C.sub.2F.sub.5.
Process H
##STR00043##
The R.sup.3 radical is as defined above.
Step a)
The compounds of the formula (XIII) can be prepared in analogy to
the process described in WO2005/55928 or Journal of Medicinal
Chemistry, 48 (2005), p. 6128-6139, by the reaction of compounds of
the formula (XI) with benzyl chlorocarbonate (benzyl chloroformate)
of the formula (XII), for example in the presence of a base.
Compounds of the formula (XI) are either commercially available or
can be prepared by known methods, for example analogously to the
processes described in WO2012/3576, WO2007/47793 or
WO2006/65703.
The conversion to compounds of the formula (XIII) can be effected
in substance or in a solvent, preference being given to conducting
the reaction in a solvent selected from customary solvents that are
inert under the prevailing reaction conditions. Preference is given
to ethers, for example diisopropyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for example
acetonitrile or propionitrile or aromatic hydrocarbons, for example
toluene or xylene.
Examples of suitable bases are inorganic bases from the group
consisting of acetates, phosphates and carbonates of alkali metals
or alkaline earth metals. Preference is given to caesium carbonate,
sodium carbonate and potassium carbonate.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
0.degree. C. to 120.degree. C.
Step b)
The compounds of the formula (IIa) can be prepared by reducing the
compounds of the formula (XIII), for example analogously to the
processes described in Journal of Heterocyclic Chemistry, 22
(1985), p. 313-318.
An example of a suitable reducing agent is lithium aluminium
hydride.
The conversion to compounds of the formula (IIa) can be effected
neat or in a solvent, preference being given to conducting the
reaction in a solvent selected from customary solvents that are
inert under the prevailing reaction conditions. Preference is given
to ethers, for example diethyl ether, diisopropyl ether, dioxane,
tetrahydrofuran, 1,2-dimethoxyethane or tert-butyl methyl
ether.
The reaction can be conducted under reduced pressure, at standard
pressure or under elevated pressure, and at temperatures of
0.degree. C. to 100.degree. C.
Also novel is the compound of the formula (II-02)
##STR00044## Methods and Uses
The invention also relates to methods for controlling animal pests,
in which compounds of the formula (I) are allowed to act on animal
pests and/or their habitat. The control of the animal pests is
preferably conducted in agriculture and forestry, and in material
protection. Preferably excluded from this are methods for the
surgical or therapeutic treatment of the human or animal body and
diagnostic methods carried out on the human or animal body.
The invention further relates to the use of the compounds of the
formula (I) as pesticides, especially crop protection agents.
In the context of the present application, the term "pesticide" in
each case also always comprises the term "crop protection
agent".
The compounds of the formula (I), given good plant tolerance,
favourable homeotherm toxicity and good environmental
compatibility, are suitable for protecting plants and plant organs
against biotic and abiotic stress factors, for increasing harvest
yields, for improving the quality of the harvested material and for
controlling animal pests, especially insects, arachnids, helminths,
nematodes and molluscs, which are encountered in agriculture, in
horticulture, in animal husbandry, in aquatic cultures, in forests,
in gardens and leisure facilities, in the protection of stored
products and of materials, and in the hygiene sector. They can
preferably be used as pesticides. They are effective against
normally sensitive and resistant species and against all or some
stages of development. The abovementioned pests include:
pests from the phylum of the Arthropoda, especially from the class
of the Arachnida, for example Acarus spp., for example Acarus siro,
Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., for
example Aculus fockeui, Aculus schlechtendali, Amblyomma spp.,
Amphitetranychus viennensis, Argas spp., Boophilus spp.,
Brevipalpus spp., for example Brevipalpus phoenicis, Bryobia
graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp.,
Dermanyssus gallinae, Dermatophagoides pteronyssinus,
Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., for
example Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus
spp., for example Eutetranychus banksi, Eriophyes spp., for example
Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor,
Hemitarsonemus spp., for example Hemitarsonemus latus
(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp.,
Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis,
Nuphersa spp., Oligonychus spp., for example Oligonychus
coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus
mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus
yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp.,
for example Panonychus citri (=Metatetranychus citri), Panonychus
ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora,
Platytetranychus multidigituli, Polyphagotarsonemus latus,
Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes
spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus
spinki, Tarsonemus spp., for example Tarsonemus confusus,
Tarsonemus pallidus, Tetranychus spp., for example Tetranychus
canadensis, Tetranychus cinnabarinus, Tetranychus turkestani,
Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp.,
Vasates lycopersici; from the class of the Chilopoda, for example
Geophilus spp., Scutigera spp.;
from the order or the class of the Collembola, for example
Onychiurus armatus; Sminthurus viridis;
from the class of the Diplopoda, for example Blaniulus
guttulatus;
from the class of the Insecta, for example from the order of the
Blattodea, for example Blatta orientalis, Blattella asahinai,
Blattella germanica, Leucophaea maderae, Panchlora spp.,
Parcoblatta spp., Periplaneta spp., for example Periplaneta
americana, Periplaneta australasiae, Supella longipalpa;
from the order of the Coleoptera, for example Acalymma vittatum,
Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes
spp., for example Agriotes linneatus, Agriotes mancus, Alphitobius
diaperinus, Amphimallon solstitialis, Anobium punctatum,
Anoplophora spp., Anthonomus spp., for example Anthonomus grandis,
Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., for
example Atomaria linearis, Attagenus spp., Baris caerulescens,
Bruchidius obtectus, Bruchus spp., for example Bruchus pisorum,
Bruchus rufimanus, Cassida spp., Cerotoma trifurcata,
Ceutorrhynchus spp., for example Ceutorrhynchus assimilis,
Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp.,
for example Chaetocnema confinis, Chaetocnema denticulata,
Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites
spp., for example Cosmopolites sordidus, Costelytra zealandica,
Ctenicera spp., Curculio spp., for example Curculio caryae,
Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes
ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,
Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus
adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica
spp., for example Diabrotica balteata, Diabrotica barberi,
Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata
undecimpunctata, Diabrotica virgifera virgifera, Diabrotica
virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus
spp., Epilachna spp., for example Epilachna borealis, Epilachna
varivestis, Epitrix spp., for example Epitrix cucumeris, Epitrix
fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis,
Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula
undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans,
Hylotrupes bajulus, Hypera postica, Hypomeces squamosus,
Hypothenemus spp., for example Hypothenemus hampei, Hypothenemus
obscurus, Hypothenemus pubescens, Lachnosterna consanguinea,
Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema
spp., Leptinotarsa decemlineata, Leucoptera spp., for example
Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp.,
Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis
spp., Melanotus spp., for example Melanotus longulus oregonensis,
Meligethes aeneus, Melolontha spp., for example Melolontha
melolontha, Migdolus spp., Monochamus spp., Naupactus
xanthographus, Necrobia spp., Niptus hololeucus, Oryctes
rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,
Otiorhynchus spp., for example Otiorhynchus cribricollis,
Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus
rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon
cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta
spp., for example Phyllotreta armoraciae, Phyllotreta pusilla,
Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica,
Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., for
example Psylliodes affinis, Psylliodes chrysocephala, Psylliodes
punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica,
Sitophilus spp., for example Sitophilus granarius, Sitophilus
linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp.,
Stegobium paniceum, Stemechus spp., for example Stemechus
paludatus, Symphyletes spp., Tanymecus spp., for example Tanymecus
dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio
molitor, Tenebrioides mauretanicus, Tribolium spp., for example
Tribolium audax, Tribolium castaneum, Tribolium confusum,
Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., for
example Zabrus tenebrioides;
from the order of the Diptera, for example Aedes spp., for example
Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans,
Agromyza spp., for example Agromyza frontella, Agromyza
parvicornis, Anastrepha spp., Anopheles spp., for example Anopheles
quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera
spp., for example Bactrocera cucurbitae, Bactrocera dorsalis,
Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala,
Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya
spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp.,
Contarinia spp., for example Contarinia johnsoni, Contarinia
nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia
sorghicola, Contarinia tritici, Cordylobia anthropophaga,
Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culex
quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp.,
Dacus oleae, Dasineura spp., for example Dasineura brassicae, Delia
spp., for example Delia antiqua, Delia coarctata, Delia florilega,
Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp.,
for example Drosphila melanogaster, Drosophila suzukii,
Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp.,
Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp.,
Hippobosca spp., Hypoderma spp., Liriomyza spp., for example
Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae,
Lucilia spp., for example Lucilia cuprina, Lutzomyia spp., Mansonia
spp., Musca spp., for example Musca domestica, Musca domestica
vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp.,
Paralauterborniella subcincta, Pegomya spp., for example Pegomya
betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp.,
Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila
rosae, Rhagoletis spp., for example Rhagoletis cingulata,
Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens,
Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium
spp., for example Simulium meridionale, Stomoxys spp., Tabanus
spp., Tetanops spp., Tipula spp., for example Tipula paludosa,
Tipula simplex;
from the order of the Hemiptera, for example Acizzia
acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida
turrita, Acyrthosipon spp., for example Acyrthosiphon pisum,
Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes
proletella, Aleurolobus barodensis, Aleurothrixus floccosus,
Allocaridara malayensis, Amrasca spp., for example Amrasca
bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.,
for example Aonidiella aurantii, Aonidiella citrina, Aonidiella
inornata, Aphanostigma piri, Aphis spp., for example Aphis
citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis
glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis
middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis
spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla
spp., Aspidiella spp., Aspidiotus spp., for example Aspidiotus
nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci,
Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus
helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla
spp., for example Cacopsylla pyricola, Calligypona marginata,
Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae,
Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis,
Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,
Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus
spp., for example Coccus hesperidum, Coccus longulus, Coccus
pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa
spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri,
Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., for
example Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae,
Dysmicoccus spp., Empoasca spp., for example Empoasca abrupta,
Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca
stevensi, Eriosoma spp., for example Eriosoma americanum, Eriosoma
lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma
spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus
coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla
spinulosa, Homalodisca coagulata, Hyalopterus arundinis,
Hyalopterus pruni, Icerya spp., for example Icerya purchasi,
Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium
spp., for example Lecanium corni (=Parthenolecanium corni),
Lepidosaphes spp., for example Lepidosaphes ulmi, Lipaphis erysimi,
Macrosiphum spp., for example Macrosiphum euphorbiae, Macrosiphum
lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp.,
Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa,
Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis,
Myzus spp., for example Myzus ascalonicus, Myzus cerasi, Myzus
ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae,
Nasonovia ribisnigri, Nephotettix spp., for example Nephotettix
cincticeps, Nephotettix nigropictus, Nilaparvata lugens,
Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla
spp., Parabemisia myricae, Paratrioza spp., for example Paratrioza
cockerelli, Parlatoria spp., Pemphigus spp., for example Pemphigus
bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus
spp., for example Phenacoccus madeirensis, Phloeomyzus passerinii,
Phorodon humuli, Phylloxera spp., for example Phylloxera
devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae,
Planococcus spp., for example Planococcus citri, Prosopidopsylla
flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona,
Pseudococcus spp., for example Pseudococcus calceolariae,
Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus
maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., for
example Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp.,
Pyrilla spp., Quadraspidiotus spp., for example Quadraspidiotus
juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus
perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp.,
for example Rhopalosiphum maidis, Rhopalosiphum oxyacanthae,
Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp.,
for example Saissetia coffeae, Saissetia miranda, Saissetia
neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis
graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp.,
Sogatella furcifera, Sogatodes spp., Stictocephala festina,
Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela
spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., for
example Toxoptera aurantii, Toxoptera citricidus, Trialeurodes
vaporariorum, Trioza spp., for example Trioza diospyri, Typhlocyba
spp., Unaspis spp., Viteus vitifolii, Zygina spp.;
from the suborder of the Heteroptera, for example Anasa tristis,
Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.,
Campylomma livida, Cavelerius spp., Cimex spp., for example Cimex
adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus,
Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops
furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., for
example Euschistus heros, Euschistus servus, Euschistus tristigmus,
Euschistus variolarius, Eurygaster spp., Halyomorpha halys,
Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa
varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus,
Lygocoris spp., for example Lygocoris pabulinus, Lygus spp., for
example Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes
excavatus, Monalonion atratum, Nezara spp., for example Nezara
viridula, Oebalus spp., Piesma quadrata, Piezodorus spp., for
example Piezodorus guildinii, Psallus spp., Pseudacysta persea,
Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea,
Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma
spp.;
from the order of the Hymenoptera, for example Acromyrmex spp.,
Athalia spp., for example Athalia rosae, Atta spp., Diprion spp.,
for example Diprion similis, Hoplocampa spp., for example
Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema
humile, Monomorium pharaonis, Sirex spp., Solenopsis invicta,
Tapinoma spp., Urocerus spp., Vespa spp., for example Vespa crabro,
Xeris spp.;
from the order of the Isopoda, for example Armadillidium vulgare,
Oniscus asellus, Porcellio scaber;
from the order of the Isoptera, for example Coptotermes spp., for
example Coptotermes formosanus, Comitermes cumulans, Cryptotermes
spp., Incisitermes spp., Microtermes obesi, Odontotermes spp.,
Reticulitermes spp., for example Reticulitermes flavipes,
Reticulitermes hesperus;
from the order of the Lepidoptera, for example Achroia grisella,
Acronicta major, Adoxophyes spp., for example Adoxophyes orana,
Aedia leucomelas, Agrotis spp., for example Agrotis segetum,
Agrotis ipsilon, Alabama spp., for example Alabama argillacea,
Amyelois transitella, Anarsia spp., Anticarsia spp., for example
Anticarsia gemmatalis, Argyroploce spp., Barathra brassicae, Borbo
cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola
spp., Cacoecia spp., Caloptilia theivora, Capua reticulana,
Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata,
Chilo spp., for example Chilo plejadellus, Chilo suppressalis,
Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp.,
Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp.,
Conotrachelus spp., Copitarsia spp., Cydia spp., for example Cydia
nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp.,
Diatraea saccharalis, Earias spp., Ecdytolopha aurantium,
Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., for
example Ephestia elutella, Ephestia kuehniella, Epinotia spp.,
Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia
ambiguella, Euproctis spp., for example Euproctis chrysorrhoea,
Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp.,
Grapholitha spp., for example Grapholita molesta, Grapholita
prunivora, Hedylepta spp., Helicoverpa spp., for example
Helicoverpa armigera, Helicoverpa zea, Heliothis spp., for example
Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma
spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata,
Laphygma spp., Leucinodes orbonalis, Leucoptera spp., for example
Leucoptera coffeella, Lithocolletis spp., for example Lithocolletis
blancardella, Lithophane antennata, Lobesia spp., for example
Lobesia botrana, Loxagrotis albicosta, Lymantria spp., for example
Lymantria dispar, Lyonetia spp., for example Lyonetia clerkella,
Malacosoma neustria, Maruca testulalis, Mamestra brassicae,
Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata,
Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp.,
Orthaga spp., Ostrinia spp., for example Ostrinia nubilalis, Oulema
melanopus, Oulema oryzae, Panolis flammea, Parnara spp.,
Pectinophora spp., for example Pectinophora gossypiella,
Perileucoptera spp., Phthorimaea spp., for example Phthorimaea
operculella, Phyllocnistis citrella, Phyllonorycter spp., for
example Phyllonorycter blancardella, Phyllonorycter crataegella,
Pieris spp., for example Pieris rapae, Platynota stultana, Plodia
interpunctella, Plusia spp., Plutella xylostella (=Plutella
maculipennis), Prays spp., Prodenia spp., Protoparce spp.,
Pseudaletia spp., for example Pseudaletia unipuncta, Pseudoplusia
includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp.,
for example Schoenobius bipunctifer, Scirpophaga spp., for example
Scirpophaga innotata, Scotia segetum, Sesamia spp., for example
Sesamia inferens, Sparganothis spp., Spodoptera spp., for example
Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda,
Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella,
Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea
cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp.,
Trichophaga tapetzella, Trichoplusia spp., for example Trichoplusia
ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.;
from the order of the Orthoptera or Saltatoria, for example Acheta
domesticus, Dichroplus spp., Gryllotalpa spp., for example
Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., for
example Locusta migratoria, Melanoplus spp., for example Melanoplus
devastator, Paratlanticus ussuriensis, Schistocerca gregaria;
from the order of the Phthiraptera, for example Damalinia spp.,
Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera
vastatrix, Phthirus pubis, Trichodectes spp.;
from the order of the Psocoptera, for example Lepinotus spp.,
Liposcelis spp.;
from the order of the Siphonaptera, for example, Ceratophyllus
spp., Ctenocephalides spp., for example Ctenocephalides canis,
Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla
cheopis;
from the order of the Thysanoptera, for example Anaphothrips
obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips
flavens, Frankliniella spp., for example Frankliniella fusca,
Frankliniella occidentalis, Frankliniella schultzei, Frankliniella
tritici, Frankliniella vaccinii, Frankliniella williamsi,
Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips
cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp.,
for example Thrips palmi, Thrips tabaci;
from the order of the Zygentoma (=Thysanura), for example
Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus,
Thermobia domestica;
from the class of the Symphyla, for example Scutigerella spp., for
example Scutigerella immaculata;
pests from the phylum of the Mollusca, for example from the class
of the Bivalvia, for example Dreissena spp.,
and also from the class of the Gastropoda, for example Arion spp.,
for example Arion ater rufus, Biomphalaria spp., Bulinus spp.,
Deroceras spp., for example Deroceras laeve, Galba spp., Lymnaea
spp., Oncomelania spp., Pomacea spp., Succinea spp.;
animal and human parasites from the phyla of the Platyhelminthes
and Nematoda, for example Aelurostrongylus spp., Amidostomum spp.,
Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala
spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia
spp., Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis
spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium
spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp.,
Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma
spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides
spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp.,
Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides
spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp.,
Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp.,
Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp.,
Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp.,
Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp.,
Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria
spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp.,
Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma
spp., Setaria spp., Spirocerca spp., Stephanofilaria spp.,
Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus
spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris
spp., Toxocara spp., Trichinella spp., Trichobilharzia spp.,
Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria
spp.;
plant pests from the phylum of the Nematoda, i.e. phytoparasitic
nematodes, especially Aglenchus spp., for example Aglenchus
agricola, Anguina spp., for example Anguina tritici, Aphelenchoides
spp., for example Aphelenchoides arachidis, Aphelenchoides
fragariae, Belonolaimus spp., for example Belonolaimus gracilis,
Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus
spp., for example Bursaphelenchus cocophilus, Bursaphelenchus
eremus, Bursaphelenchus xylophilus, Cacopaurus spp., for example
Cacopaurus pestis, Criconemella spp., for example Criconemella
curvata, Criconemella onoensis, Criconemella ornata, Criconemella
rusium, Criconemella xenoplax (=Mesocriconema xenoplax),
Criconemoides spp., for example Criconemoides ferniae,
Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., for
example Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., for
example Globodera pallida, Globodera rostochiensis, Helicotylenchus
spp., for example Helicotylenchus dihystera, Hemicriconemoides
spp., Hemicycliophora spp., Heterodera spp., for example Heterodera
avenae, Heterodera glycines, Heterodera schachtii, Hoplolaimus
spp., Longidorus spp., for example Longidorus africanus,
Meloidogyne spp., for example Meloidogyne chitwoodi, Meloidogyne
fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp.,
Nacobbus spp., Neotylenchus spp., Paraphelenchus spp.,
Paratrichodorus spp., for example Paratrichodorus minor,
Pratylenchus spp., for example Pratylenchus penetrans,
Pseudohalenchus spp., Psilenchus spp., Punctodera spp.,
Quinisulcius spp., Radopholus spp., for example Radopholus
citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus
spp., Scutellonema spp., Subanguina spp., Trichodorus spp., for
example Trichodorus obtusus, Trichodorus primitivus,
Tylenchorhynchus spp., for example Tylenchorhynchus annulatus,
Tylenchulus spp., for example Tylenchulus semipenetrans, Xiphinema
spp., for example Xiphinema index.
In addition, it is possible to control, from the sub-kingdom of the
Protozoa, the order of the Coccidia, for example Eimeria spp.
The compounds of the formula (I) can optionally, at certain
concentrations or application rates, also be used as herbicides,
safeners, growth regulators or agents to improve plant properties,
as microbicides or gametocides, for example as fungicides,
antimycotics, bactericides, virucides (including agents against
viroids) or as agents against MLO (mycoplasma-like organisms) and
RLO (rickettsia-like organisms). If appropriate, they can also be
used as intermediates or precursors for the synthesis of other
active ingredients.
Formulations
The present invention further relates to formulations and use forms
prepared therefrom as pesticides, for example drench, drip and
spray liquors, comprising at least one compound of the formula (I).
In some cases, the use forms comprise further pesticides and/or
adjuvants which improve action, such as penetrants, e.g. vegetable
oils, for example rapeseed oil, sunflower oil, mineral oils, for
example paraffin oils, alkyl esters of vegetable fatty acids, for
example rapeseed oil methyl ester or soya oil methyl ester, or
alkanol alkoxylates and/or spreaders, for example alkylsiloxanes
and/or salts, for example organic or inorganic ammonium or
phosphonium salts, for example ammonium sulphate or diammonium
hydrogenphosphate and/or retention promoters, for example dioctyl
sulphosuccinate or hydroxypropylguar polymers and/or humectants,
for example glycerol and/or fertilizers, for example ammonium-,
potassium- or phosphorus-containing fertilizers.
Customary formulations are, for example, water-soluble liquids
(SL), emulsion concentrates (EC), emulsions in water (EW),
suspension concentrates (SC, SE, FS, OD), water-dispersible
granules (WG), granules (GR) and capsule concentrates (CS); these
and further possible formulation types are described, for example,
by Crop Life International and in Pesticide Specifications, Manual
on development and use of FAO and WHO specifications for
pesticides, FAO Plant Production and Protection Papers--173,
prepared by the FAO/WHO Joint Meeting on Pesticide Specifications,
2004, ISBN: 9251048576. The formulations, in addition to one or
more compounds of the formula (I), optionally comprise further
agrochemically active ingredients.
These are preferably formulations or use forms which comprise
auxiliaries, for example extenders, solvents, spontaneity
promoters, carriers, emulsifiers, dispersants, frost protectants,
biocides, thickeners and/or further auxiliaries, for example
adjuvants. An adjuvant in this context is a component which
improves the biological activity of the formulation without having
biological activity itself. Examples of adjuvants are agents which
promote retention, the spreading characteristics, adhesion to the
leaf surface or penetration.
These formulations are prepared in a known way, for example by
mixing the compounds of the formula (I) with auxiliaries, for
example extenders, solvents and/or solid carriers and/or other
auxiliaries, for example surfactants. The formulations are produced
either in suitable facilities or else before or during
application.
The auxiliaries used may be such substances suitable for imparting
special properties, such as certain physical, technical and/or
biological properties, to the formulation of the compounds of the
formula (I), or to the use forms prepared from these formulations
(for example ready-to-use pesticides such as spray liquors or seed
dressing products).
Suitable extenders are, for example, water, polar and nonpolar
organic chemical liquids, for example from the classes of the
aromatic and non-aromatic hydrocarbons (such as paraffins,
alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and
polyols (which, if appropriate, may also be substituted, etherified
and/or esterified), the ketones (such as acetone, cyclohexanone),
esters (including fats and oils) and (poly)ethers, the
unsubstituted and substituted amines, amides, lactams (such as
N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides
(such as dimethyl sulphoxide).
If the extender utilized is water, it is also possible to use, for
example, organic solvents as auxiliary solvents. Useful liquid
solvents essentially include: aromatics such as xylene, toluene or
alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic
hydrocarbons such as chlorobenzenes, chloroethylenes or methylene
chloride, aliphatic hydrocarbons such as cyclohexane or paraffins,
for example mineral oil fractions, mineral and vegetable oils,
alcohols such as butanol or glycol and their ethers and esters,
ketones such as acetone, methyl ethyl ketone, methyl isobutyl
ketone or cyclohexanone, strongly polar solvents such as
dimethylformamide and dimethyl sulphoxide, or else water.
In principle, it is possible to use any suitable solvents. Examples
of suitable solvents are aromatic hydrocarbons, such as xylene,
toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic
hydrocarbons, such as chlorobenzene, chloroethylene or methylene
chloride, aliphatic hydrocarbons, such as cyclohexane, paraffins,
petroleum fractions, mineral and vegetable oils, alcohols, such as
methanol, ethanol, isopropanol, butanol or glycol and their ethers
and esters, ketones such as acetone, methyl ethyl ketone, methyl
isobutyl ketone or cyclohexanone, strongly polar solvents, such as
dimethyl sulphoxide, and also water.
In principle, it is possible to use all suitable carriers. Useful
carriers especially include: for example ammonium salts and ground
natural minerals such as kaolins, clays, talc, chalk, quartz,
attapulgite, montmorillonite or diatomaceous earth, and ground
synthetic minerals such as finely divided silica, alumina and
natural or synthetic silicates, resins, waxes and/or solid
fertilizers. It is likewise possible to use mixtures of such
carriers. Useful carriers for granules include: for example crushed
and fractionated natural rocks such as calcite, marble, pumice,
sepiolite, dolomite, and synthetic granules of inorganic and
organic meals, and also granules of organic material such as
sawdust, paper, coconut shells, corn cobs and tobacco stalks.
It is also possible to use liquefied gaseous extenders or solvents.
Especially suitable are those extenders or carriers which are
gaseous at standard temperature and under standard pressure, for
example aerosol propellants such as halohydrocarbons, or else
butane, propane, nitrogen and carbon dioxide.
Examples of emulsifiers and/or foam formers, dispersants or wetting
agents having ionic or nonionic properties or mixtures of these
surface-active substances are salts of polyacrylic acid, salts of
lignosulphonic acid, salts of phenolsulphonic acid or
naphthalenesulphonic acid, polycondensates of ethylene oxide with
fatty alcohols or with fatty acids or with fatty amines, with
substituted phenols (preferably alkylphenols or arylphenols), salts
of sulphosuccinic esters, taurine derivatives (preferably alkyl
taurates), phosphoric esters of polyethoxylated alcohols or
phenols, fatty acid esters of polyols, and derivatives of the
compounds containing sulphates, sulphonates and phosphates, for
example alkylaryl polyglycol ethers, alkylsulphonates, alkyl
sulphates, arylsulphonates, protein hydrolysates, lignosulphite
waste liquors and methylcellulose. The presence of a surfactant is
advantageous if one of the compounds of the formula (I) and/or one
of the inert carriers is insoluble in water and when the
application takes place in water.
Further auxiliaries which may be present in the formulations and
the use forms derived therefrom are dyes such as inorganic
pigments, for example iron oxide, titanium oxide and Prussian Blue,
and organic dyes such as alizarin dyes, azo dyes and metal
phthalocyanine dyes, and nutrients and trace nutrients such as
salts of iron, manganese, boron, copper, cobalt, molybdenum and
zinc.
In addition, stabilizers, such as low-temperature stabilizers,
preservatives, antioxidants, light stabilizers or other agents
which improve chemical and/or physical stability, may be present.
In addition, foam formers or defoamers may be present.
In addition, the formulations and the use forms derived therefrom
may also comprise, as additional auxiliaries, stickers such as
carboxymethyl cellulose and natural and synthetic polymers in the
form of powders, granules or latices, such as gum arabic, polyvinyl
alcohol and polyvinyl acetate, or else natural phospholipids such
as cephalins and lecithins and synthetic phospholipids. Further
possible auxiliaries are mineral and vegetable oils.
Optionally, yet further auxiliaries may be present in the
formulations and the use forms derived therefrom. Examples of such
additives are fragrances, protective colloids, binders, adhesives,
thickeners, thixotropic agents, penetrants, retention promoters,
stabilizers, sequestrants, complexing agents, humectants,
spreaders. In general, the compounds of the formula (I) can be
combined with any solid or liquid additive commonly used for
formulation purposes.
Useful retention promoters include all those substances which
reduce dynamic surface tension, for example dioctyl
sulphosuccinate, or increase viscoelasticity, for example
hydroxypropylguar polymers.
Useful penetrants in the present context are all those substances
which are typically used to improve the penetration of active
agrochemical ingredients into plants. Penetrants are defined in
this context by their ability to penetrate from the (generally
aqueous) application liquor and/or from the spray coating into the
cuticle of the plant and hence increase the mobility of active
ingredients in the cuticle. The method described in the literature
(Baur et al., 1997, Pesticide Science 51, 131-152) can be used for
determining this property. Examples include alcohol alkoxylates
such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate
(12), fatty acid esters, for example rapeseed oil methyl ester or
soya oil methyl ester, fatty amine alkoxylates, for example
tallowamine ethoxylate (15), or ammonium and/or phosphonium salts,
for example ammonium sulphate or diammonium hydrogenphosphate.
The formulations preferably comprise between 0.00000001% and 98% by
weight of the compound of the formula (I), with particular
preference between 0.01% and 95% by weight of the compound of the
formula (I), more preferably between 0.5% and 90% by weight of the
compound of the formula (I), based on the weight of the
formulation.
The content of the compound of the formula (I) in the use forms
prepared from the formulations (in particular pesticides) may vary
within wide ranges. The concentration of the compound of the
formula (I) in the use forms may typically be between 0.00000001%
and 95% by weight of the compound of the formula (I), preferably
between 0.00001% and 1% by weight, based on the weight of the use
form. Application is accomplished in a customary manner appropriate
for the use forms.
Mixtures
The compounds of the formula (I) can also be used in a mixture with
one or more suitable fungicides, bactericides, acaricides,
molluscicides, nematicides, insecticides, microbiological agents,
beneficial organisms, herbicides, fertilizers, bird repellents,
phytotonics, sterilants, safeners, semiochemicals and/or plant
growth regulators, in order thus, for example, to broaden the
spectrum of action, prolong the period of action, enhance the rate
of action, prevent repellency or prevent evolution of resistance.
In addition, active ingredient combinations of this kind can
improve plant growth and/or tolerance to abiotic factors, for
example high or low temperatures, to drought or to elevated water
content or soil salinity. It is also possible to improve flowering
and fruiting performance, optimize germination capacity and root
development, facilitate harvesting and improve yields, influence
maturation, improve the quality and/or the nutritional value of the
harvested products, prolong storage life and/or improve the
processability of the harvested products.
In addition, the compounds of the formula (I) may be present in a
mixture with other active ingredients or semiochemicals such as
attractants and/or bird repellents and/or plant activators and/or
growth regulators and/or fertilizers. Likewise, the compounds of
the formula (I) can be used in mixtures with agents to improve
plant properties, for example growth, yield and quality of the
harvested material.
In a particular embodiment of the invention, the compounds of the
formula (I) are in the form of formulations or the use forms
prepared from these formulations in a mixture with further
compounds, preferably those as described below.
If one of the compounds mentioned below can occur in various
tautomeric forms, these forms are also included even if not
explicitly mentioned in each case.
Insecticides/acaricides/nematicides
The active ingredients specified here with their "common names" are
known and are described for example in The Pesticide Manual,
16.sup.th ed., British Crop Protection Council 2012.
(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates,
e.g. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,
butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,
fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb,
methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb,
thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or
organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl,
azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,
chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos,
cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,
dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,
ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,
fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl
O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,
mecarbam, methamidophos, methidathion, mevinphos, monocrotophos,
naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl,
phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,
pirimiphos-methyl, profenofos, propetamphos, prothiofos,
pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos,
temephos, terbufos, tetrachlorvinphos, thiometon, triazophos,
triclorfon and vamidothion.
(2) GABA-gated chloride channel antagonists, for example
cyclodiene-organochlorines, e.g. chlordane and endosulfan or
phenylpyrazoles (fiproles), e.g. ethiprole and fipronil.
(3) Sodium channel modulators/voltage-gated sodium channel
blockers, for example pyrethroids, e.g. acrinathrin, allethrin,
d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin,
bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin,
cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin,
gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,
beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin,
cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin
[(EZ)-(1R) isomers], esfenvalerate, etofenprox, fenpropathrin,
fenvalerate, flucythrinate, flumethrin, tau-fluvalinate,
halfenprox, imiprothrin, kadethrin, permethrin, phenothrin
[(1R)-trans isomer], prallethrin, pyrethrins (pyrethrum),
resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin
[(1R) isomers)], tralomethrin and transfluthrin or DDT or
methoxychlor.
(4) Nicotinergic acetylcholine receptor (nAChR) agonists, for
example neonicotinoids, e.g. acetamiprid, clothianidin,
dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam
or nicotine or sulfoxaflor.
(5) Allosteric activators of the nicotinergic acetylcholine
receptor (nAChR), for example spinosyns, e.g. spinetoram and
spinosad.
(6) Chloride channel activators, for example,
avermectins/milbemycins, e.g. abamectin, emamectin benzoate,
lepimectin and milbemectin.
(7) Juvenile hormone imitators, for example, juvenile hormone
analogues e.g. hydroprene, kinoprene and methoprene or fenoxycarb
or pyriproxyfen.
(8) Active ingredients with unknown or nonspecific mechanisms of
action, for example
alkyl halides, e.g. methyl bromide and other alkyl halides; or
chloropicrine or sulphuryl fluoride or borax or tartar emetic.
(9) Selective antifeedants, e.g. pymetrozine or flonicamid.
(10) Mite growth inhibitors, e.g. clofentezine, hexythiazox and
diflovidazin or etoxazole.
(11) Microbial disruptors of the insect gut membrane, e.g. Bacillus
thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus
thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies
kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT
plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab,
Cry3Bb, Cry34/35Ab1.
(12) Oxidative phosphorylation inhibitors, ATP disruptors, for
example diafenthiuron or organotin compounds, e.g. azocyclotin,
cyhexatin and fenbutatin oxide or propargite or tetradifon.
(13) Oxidative phosphorylation decouplers that interrupt the H
proton gradient, for example chlorfenapyr, DNOC and
sulfluramid.
(14) Nicotinergic acetylcholine receptor antagonists, for example
bensultap, cartap hydrochloride, thiocyclam, and
thiosultap-sodium.
(15) Chitin biosynthesis inhibitors, type 0, for example
bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,
flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,
teflubenzuron and triflumuron.
(16) Chitin biosynthesis inhibitors, type 1, for example
buprofezin.
(17) Moulting inhibitors (especially for Diptera, i.e. dipterans),
for example cyromazine.
(18) Ecdysone receptor agonists, for example chromafenozide,
halofenozide, methoxyfenozide and tebufenozide.
(19) Octopaminergic agonists, for example amitraz.
(20) Complex-III electron transport inhibitors, for example
hydramethylnon or acequinocyl or fluacrypyrim.
(21) Complex-I electron transport inhibitors, for example METI
acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,
tebufenpyrad and tolfenpyrad or rotenone (Derris).
(22) Voltage-gated sodium channel blockers, for example indoxacarb
or metaflumizone.
(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic and
tetramic acid derivatives, e.g. spirodiclofen, spiromesifen and
spirotetramat.
(24) Complex-IV electron transport inhibitors, for example
phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine
and zinc phosphide or cyanide.
(25) Complex-II electron transport inhibitors, for example
cyenopyrafen and cyflumetofen.
(28) Ryanodine receptor effectors, for example diamides, e.g.
chlorantraniliprole, cyantraniliprole and flubendiamide,
further active ingredients, for example afidopyropen, azadirachtin,
benclothiaz, benzoximate, bifenazate, bromopropylate,
chinomethionat, cryolite,
dicofol, diflovidazin, fluensulfone, flometoquin, flufenerim,
flufenoxystrobin, flufiprole, fluopyram, flupyradifurone,
fufenozide, heptafluthrin, imidaclothiz, iprodione, meperfluthrin,
paichongding, pyflubumide, pyrifluquinazon, pyriminostrobin,
tetramethylfluthrin and iodomethane; and also preparations based on
Bacillus firmus (I-1582, BioNeem, Votivo), and also the following
compounds:
3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-
-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from
WO2005/077934) and
1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(tr-
ifluoromethyl)-1H-1,2,4-triazole-5-amine (known from
WO2006/043635),
{1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro
[indole-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone
(known from WO2003/106457),
2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-
-(trifluoromethyl)phenyl]isonicotinamide (known from
WO2006/003494),
3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2--
one (known from WO2009/049851),
3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-e-
thylcarbonate (known from WO2009/049851),
4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine
(known from WO2004/099160),
4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from
WO2003/076415), PF1364 (CAS Reg. No. 1204776-60-2),
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl-
]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide
(known from WO2005/085216),
4-{5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-
-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphtha-
mide (known from WO2009/002809), methyl
2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)--
5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from
WO2005/085216), methyl
2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)--
5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate (known from
WO2005/085216), methyl
2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbony
1}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate
(known from WO2005/085216), methyl
2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carb-
onyl}amino)benzoyl]-2-ethylhydrazinecarboxylate (known from
WO2005/085216),
1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-
-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide
(known from WO2010/069502),
N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(-
3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from
CN102057925),
3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-y-
l)-2-methylphenyl]phthalamide (known from WO2012/034472),
8-chloro-N-[(2-chloro-5-methoxyphenyl)sulphonyl]-6-(trifluoromethyl)imida-
zo[1,2-a]pyridine-2-carboxamide (known from WO2010/129500),
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl-
]-2-methyl-N-(1-oxidothietan-3-yl)benzamide (known from
WO2009/080250),
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl-
]-2-methyl-N-(1-oxidothietan-3-yl)benzamide (known from
WO2012/029672),
1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyri-
midin-1-ium-2-olate (known from WO2009/099929),
1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-
-1-ium-2-olate (known from WO2009/099929),
(5S,8R)-1-[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-1H-
-5,8-epoxyimidazo[1,2-a]azepine (known from WO2010/069266),
(2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarb-
oximidamide (known from WO2010/060231),
4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2--
methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940),
N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2--
yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from
WO2008/134969).
Fungicides
The active ingredients specified herein by their common name are
known and described, for example, in the "Pesticide Manual".
(1) Ergosterol biosynthesis inhibitors, for example (1.1)
aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4)
bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7)
difenoconazole, (1.8) diniconazole, (1.9) diniconazole-M, (1.10)
dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13)
etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16)
fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19)
fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22)
flutriafole, (1.23) furconazole, (1.24) furconazole-cis, (1.25)
hexaconazole, (1.26) imazalil, (1.27) imazalil sulphate, (1.28)
imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31)
myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34)
oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37)
penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40)
propiconazole, (1.41) prothioconazole, (1.42) pyributicarb, (1.43)
pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46)
spiroxamine, (1.47) tebuconazole, (1.48) terbinafin, (1.49)
tetraconazole, (1.50) triadimefon, (1.51) triadimenol, (1.52)
tridemorph, (1.53) triflumizole, (1.54) triforine, (1.55)
triticonazole, (1.56) uniconazole, (1.57) uniconazole-P, (1.58)
viniconazole, (1.59) voriconazole, (1.60)
1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61)
methyl
1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,
(1.62)
N'-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]pheny-
l}-N-ethyl-N-methylimidoformamide,
(1.63)N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsi-
lyl)propoxy]phenyl}imidoformamide and (1.64)
O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioa-
te, (1.65) pyrisoxazole.
(2) Respiration inhibitors (respiratory chain inhibitors), for
example (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4)
diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil,
(2.8) fluxapyroxad, (2.9) furametpyr, (2.10) furmecyclox, (2.11)
isopyrazam mixture of the syn-epimeric racemate 1RS,4SR,9RS and the
anti-empimeric racemate 1RS,4SR,9SR, (2.12) isopyrazam
(anti-epimeric racemate), (2.13) isopyrazam (anti-epimeric
enantiomer 1R,4S,9S), (2.14) isopyrazam (anti-epimeric enantiomer
1S,4R,9R), (2.15) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS),
(2.16) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.17)
isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18) mepronil,
(2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad, (2.22)
sedaxane, (2.23) thifluzamide, (2.24)
1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-p-
yrazole-4-carboxamide, (2.25)
3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-py-
razole-4-carboxamide, (2.26)
3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-
-methyl-1H-pyrazole-4-carboxamide,
(2.27)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)--
1-methyl-1H-pyrazole-4-carboxamide, (2.28)
5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}pheny-
l)ethyl]quinazoline-4-amine, (2.29) benzovindiflupyr,
(2.30)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaph-
thalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
and
(2.31)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaph-
thalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,
(2.32)
3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-
-1H-pyrazole-4-carboxamide, (2.33)
1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-
-4-carboxamide, (2.34)
1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl-
)-1H-pyrazole-4-carboxamide, (2.35)
1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-
-4-yl]-1H-pyrazole-4-carboxamide, (2.36)
1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-
-4-yl]-1H-pyrazole-4-carboxamide, (2.37)
3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden--
4-yl]-1H-pyrazole-4-carboxamide, (2.38)
3-(difluoromethyl)-1-methyl-N-[(3R)-1,
1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,
(2.39)
1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-
-1H-pyrazole-4-carboxamide, (2.40)
1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyr-
azole-4-carboxamide, (2.41) benodanil, (2.42)
2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxam-
ide, (2.43) isofetamid
(3) Respiration inhibitors (respiratory chain inhibitors) that act
on complex III of the respiratory chain, for example (3.1)
ametoctradin, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4)
cyazofamid, (3.5) coumethoxystrobin, (3.6) coumoxystrobin, (3.5)
dimoxystrobin, (3.8) enestroburin, (3.9) famoxadone, (3.10)
fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13)
kresoxim-methyl, (3.14) metominostrobin, (3.15) orysastrobin,
(3.16) picoxystrobin, (3.17) pyraclostrobin, (3.18)
pyrametostrobin, (3.19) pyraoxystrobin, (3.20) pyribencarb, (3.21)
triclopyricarb, (3.22) trifloxystrobin, (3.23)
(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}pheny-
l)-2-(methoxyimino)-N-methylethanamide, (3.24)
(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl-
]ethylidene}amino)oxy]methyl}phenyl)ethanamide, (3.25)
(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]e-
thoxy}imino)methyl]phenyl}ethanamide, (3.26)
(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylid-
ene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,
(3.27)
(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)-
methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, (3.28)
2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxam-
ide, (3.29)
5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}-
amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (3.30)
methyl
(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulphanyl)methyl]p-
henyl}-3-methoxyprop-2-enoate,
(3.31)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenz-
amide, (3.32)
2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide
(4) inhibitors of mitosis and cell division, for example (4.1)
benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4)
diethofencarb, (4.5) ethaboxam, (4.6) fluopicolid, (4.7)
fuberidazole, (4.8) pencycuron, (4.9) thiabendazole, (4.10)
thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13)
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triaz-
olo[1,5-a]pyrimidine and (4.14)
3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyrid-
azine.
(5) Compounds having multisite activity, for example (5.1) Bordeaux
mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil, (5.5)
copper preparations such as copper hydroxide, (5.6) copper
naphthenate, (5.7) copper oxide, (5.8) copper oxychloride, (5.9)
copper sulphate, (5.10) dichlofluanid, (5.11) dithianon, (5.12)
dodine, (5.13) dodine free base, (5.14) ferbam, (5.15) fluorfolpet,
(5.16) folpet, (5.17) guazatine, (5.18) guazatine acetate, (5.19)
iminoctadine, (5.20) iminoctadine albesilate, (5.21) iminoctadine
triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) maneb, (5.25)
metiram, (5.26) zinc metiram, (5.27) copper-oxine, (5.28)
propamidine, (5.29) propineb, (5.30) sulphur and sulphur
preparations, for example calcium polysulphide, (5.31) thiram,
(5.32) tolylfluanid, (5.33) zineb, (5.34) ziram and (5.35)
anilazine.
(6) Resistance inducers, for example (6.1) acibenzolar-S-methyl,
(6.2) isotianil, (6.3) probenazole, (6.4) tiadinil and (6.5)
laminarin.
(7) Amino acid and protein biosynthesis inhibitors, for example
(7.1) andoprim, (7.2) blasticidin-S, (7.3) cyprodinil, (7.4)
kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6)
mepanipyrim, (7.7) pyrimethanil, (7.8)
3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoli-
ne and (7.9) oxytetracycline and (7.10) streptomycin.
(8) ATP production inhibitors, for example (8.1) fentin acetate,
(8.2) fentin chloride, (8.3) fentin hydroxide and (8.4)
silthiofam.
(9) Cell wall synthesis inhibitors, for example (9.1)
benthiavalicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4)
iprovalicarb, (9.5) mandipropamid, (9.6) polyoxins, (9.7)
polyoxorim, (9.8) validamycin A, (9.9) valifenalate and (9.10)
polyoxin B.
(10) Lipid and membrane synthesis inhibitors, for example (10.1)
biphenyl, (10.2) chlorneb, (10.3) dicloran, (10.4) edifenphos,
(10.5) etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8)
isoprothiolane, (10.9) propamocarb, (10.10) propamocarb
hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos, (10.13)
quintozene, (10.14) tecnazene and (10.15) tolclofos-methyl.
(11) Melanin biosynthesis inhibitors, for example (11.1)
carpropamid, (11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide,
(11.5) pyroquilon, (11.6) tricyclazole and (11.7)
2,2,2-trifluoroethyl
{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.
(12) Nucleic acid synthesis inhibitors, for example (12.1)
benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate,
(12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7)
furalaxyl, (12.8) hymexazole, (12.9) metalaxyl, (12.10) metalaxyl-M
(mefenoxam), (12.11) ofurace, (12.12) oxadixyl, (12.13) oxolinic
acid and (12.14) octhilinone.
(13) Signal transduction inhibitors, for example (13.1)
chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4)
iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7)
vinclozolin and (13.8) proquinazid.
(14) Decouplers, for example (14.1) binapacryl, (14.2) dinocap,
(14.3) ferimzone, (14.4) fluazinam and (14.5) meptyldinocap.
(15) Further compounds, for example (15.1) benthiazole, (15.2)
bethoxazine, (15.3) capsimycin, (15.4) carvone, (15.5)
chinomethionat, (15.6) pyriofenone (chlazafenone), (15.7) cufraneb,
(15.8) cyflufenamid, (15.9) cymoxanil, (15.10) cyprosulfamide,
(15.11) dazomet, (15.12) debacarb, (15.13) dichlorophen, (15.14)
diclomezine, (15.15) difenzoquat, (15.16) difenzoquat
methylsulphate, (15.17) diphenylamine, (15.18) EcoMate, (15.19)
fenpyrazamine, (15.20) flumetover, (15.21) fluorimid, (15.22)
flusulfamide, (15.23) flutianil, (15.24) fosetyl-aluminium, (15.25)
fosetyl-calcium, (15.26) fosetyl-sodium, (15.27) hexachlorobenzene,
(15.28) irumamycin, (15.29) methasulfocarb, (15.30) methyl
isothiocyanate, (15.31) metrafenone, (15.32) mildiomycin, (15.33)
natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35)
nitrothal-isopropyl, (15.36) octhilinone, (15.37) oxamocarb,
(15.38) oxyfenthiin, (15.39) pentachlorophenol and its salts,
(15.40) phenothrin, (15.41) phosphoric acid and its salts, (15.42)
propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44)
pyrimorph, (15.45)
(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)pr-
op-2-en-1-one, (15.46)
(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)pr-
op-2-en-1-one, (15.47) pyrrolnitrin, (15.48) tebufloquin, (15.49)
tecloftalam, (15.50) tolnifanide, (15.51) triazoxide, (15.52)
trichlamide, (15.53) zarilamid, (15.54)
(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-
-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl
2-methylpropanoate, (15.55)
1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thi-
azol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-
ethanone, (15.56)
1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thi-
azol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-
ethanone, (15.57)
1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol--
2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethan-
one, (15.58) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl
1H-imidazole-1-carboxylate, (15.59)
2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, (15.60)
2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61)
2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-te-
trone, (15.62)
2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4-
,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,
(15.63)
2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5--
phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethano-
ne, (15.64)
2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-di-
hydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,
(15.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.66)
2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazo-
l-5-yl]pyridine, (15.67) 2-phenylphenol and salts, (15.68)
3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,
(15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70)
3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,
(15.71)
4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,
(15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73)
5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,
(15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.75)
5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.76)
5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (15.77)
ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.78)
N'-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-
-N-ethyl-N-methylimidoformamide,
(15.79)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propan-
amide,
(15.80)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn--
1-yloxy)phenyl]propanamide,
(15.81)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,
(15.82)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide-
,
(15.83)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotina-
mide,
(15.84)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-di-
fluorophenyl]methyl}-2-phenylacetamide,
(15.85)N--{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluo-
rophenyl]methyl}-2-phenylacetamide, (15.86)
N'-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylpheny-
l}-N-ethyl-N-methylimidoformamide,
(15.87)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acety-
l}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-car-
boxamide,
(15.88)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-
-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3--
thiazole-4-carboxamide,
(15.89)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acety-
l}piperidin-4-yl)-N-[(1
S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,
(15.90) pentyl
{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)meth-
yl]pyridin-2-yl}carbamate, (15.91) phenazine-1-carboxylic acid,
(15.92) quinolin-8-ol, (15.93) quinolin-8-ol sulphate (2:1),
(15.94) tert-butyl
{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyri-
din-2-yl}carbamate, (15.95)
1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyr-
azole-4-carboxamide,
(15.96)N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-
-4-carboxamide,
(15.97)N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyr-
azole-4-carboxamide, (15.98)
3-(difluoromethyl)-1-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-1H-pyra-
zole-4-carboxamide,
(15.99)N-(2',5'-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-py-
razole-4-carboxamide, (15.100)
3-(difluoromethyl)-1-methyl-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyraz-
ole-4-carboxamide, (15.101)
5-fluoro-1,3-dimethyl-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4--
carboxamide, (15.102)
2-chloro-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (15.103)
3-(difluoromethyl)-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-meth-
yl-1H-pyrazole-4-carboxamide,
(15.104)N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dime-
thyl-1H-pyrazole-4-carboxamide, (15.105)
3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-car-
boxamide,
(15.106)N-(4'-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyr-
azole-4-carboxamide, (15.107)
2-chloro-N-(4'-ethynylbiphenyl-2-yl)nicotinamide, (15.108)
2-chloro-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,
(15.109)
4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl-
]-1,3-thiazole-5-carboxamide, (15.110)
5-fluoro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimeth-
yl-1H-pyrazole-4-carboxamide, (15.111)
2-chloro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamid-
e, (15.112)
3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]--
1-methyl-1H-pyrazole-4-carboxamide, (15.113)
5-fluoro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimeth-
yl-1H-pyrazole-4-carboxamide, (15.114)
2-chloro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamid-
e, (15.115)
(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)-
methanone,
(15.116)N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-metho-
xyphenyl)ethyl]-N2-(methylsulphonyl)valinamide, (15.117)
4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.118) but-3-yn-1-yl
{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-
pyridin-2-yl}carbamate, (15.119) 4-amino-5-fluoropyrimidin-2-ol
(tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.120)
propyl 3,4,5-trihydroxybenzoate, (15.121)
1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4--
carboxamide, (15.122)
1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazo-
le-4-carboxamide, (15.123)
1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazo-
le-4-carboxamide, (15.124)
[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyri-
din-3-yl)methanol, (15.125)
(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](-
pyridin-3-yl)methanol, (15.126)
(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](-
pyridin-3-yl)methanol, (15.127)
2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihy-
dro-3H-1,2,4-triazole-3-thione, (15.128)
1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-
-triazol-5-yl thiocyanate, (15.129)
5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2--
yl]methyl}-1H-1,2,4-triazole, (15.130)
2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihyd-
ro-3H-1,2,4-triazole-3-thione, (15.131) 2-{[rel(2R,3
S)-3-(2-chlorophenyl)-2-(2,4-difluoropheny)xiran-2-yl]methyl}-2,4-dihydro-
-3H-1,2,4-triazole-3-thione, (15.132)
2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methy-
l}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.133) 1-{[rel(2R,3
S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4--
triazol-5-yl thiocyanate, (15.134)
1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methy-
l}-1H-1,2,4-triazol-5-yl thiocyanate, (15.135)
5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluoropheny-
l)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (15.136)
5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluoropheny-
l)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (15.137)
2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.138)
2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.139)
2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.140)
2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.141)
2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.142)
2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.143)
2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.144) 2-[(2S,4R,5
S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihyd-
ro-3H-1,2,4-triazole-3-thione, (15.145)
2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl-
)benzamide, (15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147)
2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,
(15.148)
3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoli-
ne, (15.149) abscisic acid, (15.150)
3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan--
2-yl]-1H-pyrazole-4-carboxamide, (15.151)
N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethy-
l-N-methylimidoformamide, (15.152)
N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethy-
l-N-methylimidoformamide, (15.153)
N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-
-ethyl-N-methylimidoformamide, (15.154)
N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-
-ethyl-N-methylimidoformamide, (15.155)
N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-et-
hyl-N-methy limidoformamide, (15.156)
N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N--
ethyl-N-methylimidoformamide,
(15.157)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-
-methyl-1H-pyrazole-4-carboxamide,
(15.158)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-
-1-methyl-1H-pyrazole-4-carboxamide,
(15.159)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro--
1-methyl-1H-pyrazole-4-carboxamide,
(15.160)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-flu-
oro-1-methyl-1H-pyrazole-4-carboxamide,
(15.161)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-
-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.162)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-flu-
oro-1-methyl-1H-pyrazole-4-carboxamide, (15.163)
N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)--
1-methyl-1H-pyrazole-4-carboxamide,
(15.164)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-
-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.165)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-
-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.166)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropyl-
benzyl)-1-methyl-1H-pyrazole-4-carboxamide,
(15.167)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-flu-
oro-1-methyl-H-pyrazole-4-carboxamide,
(15.168)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methyl-
benzyl)-1-methyl-1H-pyrazole-4-carboxamide,
(15.169)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-
-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.170)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)--
5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.171)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluorom-
ethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.172)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2--
(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,
(15.173)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluorom-
ethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.174)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(-
difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.175)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-
-fluoro-1-methyl-1H-pyrazole-4-carboxamide,
(15.176)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-
-methyl-1H-pyrazol-4-carbothioamide, (15.177)
3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-
-1-methyl-1H-pyrazole-4-carboxamide, (15.178)
3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden--
4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (15.179)
3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden--
4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (15.180)
N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,
(15.181)
N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-
-ethyl-N-methylimidoformamide,
(15.182)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-d-
imethyl-1H-pyrazole-5-amine. All the mixing components mentioned in
classes (1) to (15), as the case may be, may form salts with
suitable bases or acids if they are capable of doing so on the
basis of their functional groups.
Biological Pesticides as Mixing Components
The compounds of the formula (I) can be combined with biological
pesticides.
Biological pesticides include especially bacteria, fungi, yeasts,
plant extracts and products formed by microorganisms, including
proteins and secondary metabolites.
Biological pesticides include bacteria such as spore-forming
bacteria, root-colonizing bacteria and bacteria which act as
biological insecticides, fungicides or nematicides.
Examples of such bacteria which are used or can be used as
biological pesticides are:
Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus
cereus, especially B. cereus strain CNCM 1-1562 or Bacillus firmus,
strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus,
especially strain GB34 (Accession No. ATCC 700814) and strain
QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis,
especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus
subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus
subtilis strain OST 30002 (Accession No. NRRL B-50421) Bacillus
thuringiensis, especially B. thuringiensis subspecies israelensis
(serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B.
thuringiensis subsp. aizawai, especially strain ABTS-1857
(SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B.
thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria
penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3
(Accession Number ATCC SD-5834), Streptomyces microflavus strain
AQ6121 (=QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ
6047 (Accession Number NRRL 30232).
Examples of fungi and yeasts which are used or can be used as
biological pesticides are:
Beauveria bassiana, especially strain ATCC 74040, Coniothyrium
minitans, especially strain CON/M/91-8 (Accession No. DSM-9660),
Lecanicillium spp., especially strain HRO LEC 12, Lecanicillium
lecanii, (formerly known as Verticillium lecanii), especially
strain KV01, Metarhizium anisopliae, especially strain F52
(DSM3884/ATCC 90448), Metschnikowia fructicola, especially strain
NRRL Y-30752, Paecilomyces fumosoroseus (now: Isaria fumosorosea),
especially strain IFPC 200613, or strain Apopka 97 (Accesion No.
ATCC 20874), Paecilomyces lilacinus, especially P. lilacinus strain
251 (AGAL 89/030550), Talaromyces flavus, especially strain V117b,
Trichoderma atroviride, especially strain SC1 (Accession Number CBS
122089), Trichoderma harzianum, especially T. harzianum rifai T39
(Accession Number CNCM 1-952).
Examples of viruses which are used or can be used as biological
pesticides are:
Adoxophyes orana (summer fruit tortrix) granulosis virus (GV),
Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa
armigera (cotton bollworm) nuclear polyhedrosis virus (NPV),
Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall
armyworm) mNPV, Spodoptera littoralis (African cotton leafworm)
NPV.
Also included are bacteria and fungi which are added as `inoculant`
to plants or plant parts or plant organs and which, by virtue of
their particular properties, promote plant growth and plant health.
Examples include:
Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,
Azotobacter spp., Bradyrhizobium spp., Burkholderia spp.,
especially Burkholderia cepacia (formerly known as Pseudomonas
cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp.,
Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus
tinctorus, Pseudomonas spp., Rhizobium spp., especially Rhizobium
trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp.,
Streptomyces spp.
Examples of plant extracts and products formed by microorganisms,
including proteins and secondary metabolites, which are used or can
be used as biological pesticides are:
Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP,
Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum,
chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense,
Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin
extract), pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja,
Regalia, "Requiem.TM. Insecticide", rotenone, ryania/ryanodine,
Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon,
Tropaeulum majus, Urtica dioica, Veratrin, Viscum album,
Brassicaceae extract, especially oilseed rape powder or mustard
powder.
Safeners as Mixing Components
The compounds of the formula (I) can be combined with safeners, for
example benoxacor, cloquintocet (-mexyl), cyometrinil,
cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim,
flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr
(-diethyl), naphthalic anhydride, oxabetrinil,
2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide
(CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane
(CAS 71526-07-3),
2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS
52836-31-4).
Plants and Plant Parts
All plants and parts of plants can be treated in accordance with
the invention. Plants are understood here to mean all plants and
populations of plants, such as desirable and undesirable wild
plants or crop plants (including naturally occurring crop plants),
for example cereals (wheat, rice, triticale, barley, rye, oats),
maize, soya bean, potato, sugar beet, sugar cane, tomatoes, peas
and other vegetable species, cotton, tobacco, oilseed rape, and
also fruit plants (with the fruits apples, pears, citrus fruits and
grapevines). Crop plants may be plants which can be obtained by
conventional breeding and optimization methods or by
biotechnological and genetic engineering methods or combinations of
these methods, including the transgenic plants and including the
plant cultivars which are protectable or non-protectable by plant
breeders' rights. Parts of plants shall be understood to mean all
parts and organs of the plants above and below ground, such as
shoot, leaf, flower and root, examples given being leaves, needles,
stalks, stems, flowers, fruit bodies, fruits and seeds, and also
tubers, roots and rhizomes. Parts of plants also include harvested
material and vegetative and generative propagation material, for
example cuttings, tubers, rhizomes, slips and seeds.
Treatment according to the invention of the plants and plant parts
with the compounds of the formula (I) is carried out directly or by
allowing the compounds to act on their surroundings, environment or
storage space by the customary treatment methods, for example by
immersion, spraying, evaporation, fogging, scattering, painting on,
injection and, in the case of propagation material, in particular
in the case of seeds, also by applying one or more coats.
As already mentioned above, it is possible to treat all plants and
their parts according to the invention. In a preferred embodiment,
wild plant species and plant cultivars, or those obtained by
conventional biological breeding, such as crossing or protoplast
fusion, and parts thereof, are treated. In a further preferred
embodiment, transgenic plants and plant cultivars obtained by
genetic engineering methods, if appropriate in combination with
conventional methods (genetically modified organisms), and parts
thereof are treated. The term "parts" or "parts of plants" or
"plant parts" has been explained above. Particular preference is
given in accordance with the invention to treating plants of the
respective commercially customary cultivars or those that are in
use. Plant cultivars are understood to mean plants having new
properties ("traits") and which have been obtained by conventional
breeding, by mutagenesis or by recombinant DNA techniques. They may
be cultivars, varieties, biotypes or genotypes.
Transgenic Plants, Seed Treatment and Integration Events
The preferred transgenic plants or plant cultivars (those obtained
by genetic engineering) which are to be treated in accordance with
the invention include all plants which, through the genetic
modification, received genetic material which imparts particular
advantageous useful properties ("traits") to these plants. Examples
of such properties are better plant growth, increased tolerance to
high or low temperatures, increased tolerance to drought or to
levels of water or soil salinity, enhanced flowering performance,
easier harvesting, accelerated ripening, higher yields, higher
quality and/or higher nutritional value of the harvested products,
better storage life and/or processibility of the harvested
products. Further and particularly emphasized examples of such
properties are increased resistance of the plants against animal
and microbial pests, such as insects, arachnids, nematodes, mites,
slugs and snails owing, for example, to toxins formed in the
plants, in particular those produced in the plants by the genetic
material from Bacillus thuringiensis (for example by the genes
CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c
Cry2Ab, Cry3Bb and CryIF and also combinations thereof), and also
increased resistance of the plants against phytopathogenic fungi,
bacteria and/or viruses caused, for example, by systemic acquired
resistance (SAR), systemin, phytoalexins, elicitors and resistance
genes and correspondingly expressed proteins and toxins, and also
increased tolerance of the plants to certain herbicidally active
ingredients, for example imidazolinones, sulphonylureas,
glyphosates or phosphinothricin (for example the "PAT" gene). The
genes which impart the desired properties ("traits") in question
may also be present in combinations with one another in the
transgenic plants. Examples of transgenic plants include the
important crop plants, such as cereals (wheat, rice, triticale,
barley, rye, oats), maize, soya beans, potatoes, sugar beet, sugar
cane, tomatoes, peas and other types of vegetable, cotton, tobacco,
oilseed rape and also fruit plants (with the fruits apples, pears,
citrus fruits and grapes), particular emphasis being given to
maize, soya beans, wheat, rice, potatoes, cotton, sugar cane,
tobacco and oilseed rape. Properties ("traits") which are
particularly emphasized are the increased resistance of the plants
to insects, arachnids, nematodes and slugs and snails.
Crop Protection--Types of Treatment
The treatment of the plants and plant parts with the compounds of
the formula (I) is carried out directly or by action on their
surroundings, habitat or storage space using customary treatment
methods, for example by dipping, spraying, atomizing, irrigating,
evaporating, dusting, fogging, broadcasting, foaming, painting,
spreading-on, injecting, watering (drenching), drip irrigating and,
in the case of propagation material, in particular in the case of
seed, furthermore as a powder for dry seed treatment, a solution
for liquid seed treatment, a water-soluble powder for slurry
treatment, by incrusting, by coating with one or more coats, etc.
It is furthermore possible to apply the compounds of the formula
(I) by the ultra-low volume method or to inject the application
form or the compound of the formula (I) itself into the soil.
A preferred direct treatment of the plants is foliar application,
i.e. compounds of the formula (I) are applied to the foliage, where
treatment frequency and the application rate should be adjusted
according to the level of infestation with the pest in
question.
In the case of systemically active compounds, the compounds of the
formula (I) also access the plants via the root system. The plants
are then treated by the action of the compounds of the formula (I)
on the habitat of the plant. This can be accomplished, for example,
by drenching, or by mixing into the soil or the nutrient solution,
meaning that the locus of the plant (e.g. soil or hydroponic
systems) is impregnated with a liquid form of the compounds of the
formula (I), or by soil application, meaning that the compounds of
the formula (I) are introduced in solid form (e.g. in the form of
granules) into the locus of the plants. In the case of paddy rice
crops, this can also be accomplished by metering the compound of
the formula (I) in a solid application form (for example as
granules) into a flooded paddy field.
Seed Treatment
The control of animal pests by the treatment of the seed of plants
has long been known and is the subject of constant improvements.
Nevertheless, the treatment of seed gives rise to a series of
problems which cannot always be solved in a satisfactory manner.
Thus, it is desirable to develop methods for protecting the seed
and the germinating plant which dispense with, or at least reduce
considerably, the additional application of pesticides during
storage, after sowing or after emergence of the plants. It is
additionally desirable to optimize the amount of active ingredient
used so as to provide optimum protection for the seed and the
germinating plant from attack by animal pests, but without damage
to the plant itself by the active ingredient used. In particular,
methods for the treatment of seed should also take account of the
intrinsic insecticidal or nematicidal properties of pest-resistant
or -tolerant transgenic plants in order to achieve optimal
protection of the seed and the germinating plant with a minimum
expenditure of pesticides.
The present invention therefore in particular also relates to a
method for the protection of seed and germinating plants, from
attack by pests, by treating the seed with one of the compounds of
the formula (I). The inventive method for protecting seed and
germinating plants against attack by pests further comprises a
method in which the seed is treated simultaneously in one operation
or sequentially with a compound of the formula (I) and a mixing
component. It also further comprises a method where the seed is
treated at different times with a compound of the formula (I) and a
mixing component.
The invention likewise relates to the use of the compounds of the
formula (I) for the treatment of seed for protecting the seed and
the resulting plant from animal pests.
The invention further relates to seed which has been treated with a
compound of the formula (I) for protection from animal pests. The
invention also relates to seed which has been treated
simultaneously with a compound of the formula (I) and a mixing
component. The invention further relates to seed which has been
treated at different times with a compound of the formula (I) and a
mixing component. In the case of seed which has been treated at
different times with a compound of the formula (I) and a mixing
component, the individual substances may be present on the seed in
different layers. In this case, the layers comprising a compound of
the formula (I) and a mixing component may optionally be separated
by an intermediate layer. The invention also relates to seed in
which a compound of the formula (I) and a mixing component have
been applied as part of a coating or as a further layer or further
layers in addition to a coating.
The invention further relates to seed which, after the treatment
with a compound of the formula (I), is subjected to a film-coating
process to prevent dust abrasion on the seed.
One of the advantages that occurs when one of the compounds of the
formula (I) acts systemically is that the treatment of the seed
protects not just the seed itself but also the plants resulting
therefrom after emergence against animal pests. In this way, the
immediate treatment of the crop at the time of sowing or shortly
thereafter can be dispensed with.
A further advantage is that the treatment of the seed with a
compound of the formula (I) can enhance germination and emergence
of the treated seed.
It is likewise considered to be advantageous that compounds of the
formula (I) can especially also be used for transgenic seed.
In addition, compounds of the formula (I) can be used in
combination with signalling technology compositions, which results
in better colonization by symbionts, for example rhizobia,
mycorrhizae and/or endophytic bacteria or fungi, and/or leads to
optimized nitrogen fixation.
The compounds of the formula (I) are suitable for protection of
seed of any plant variety which is used in agriculture, in
greenhouses, in forests or in horticulture. More particularly, this
includes seed of cereals (for example wheat, barley, rye, millet
and oats), maize, cotton, soya beans, rice, potatoes, sunflowers,
coffee, tobacco, canola, oilseed rape, beets (for example
sugarbeets and fodder beets), peanuts, vegetables (for example
tomatoes, cucumbers, beans, cruciferous vegetables, onions and
lettuce), fruit plants, lawns and ornamental plants. Of particular
significance is the treatment of the seed of cereals (such as
wheat, barley, rye and oats), maize, soya, cotton, canola, oilseed
rape and rice.
As already mentioned above, the treatment of transgenic seed with a
compound of the formula (I) is also of particular importance. This
involves the seed of plants which generally contain at least one
heterologous gene which controls the expression of a polypeptide
having insecticidal and/or nematicidal properties in particular.
The heterologous genes in transgenic seed may originate from
microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia,
Trichoderma, Clavibacter, Glomus or Gliocladium. The present
invention is particularly suitable for the treatment of transgenic
seed containing at least one heterologous gene originating from
Bacillus sp. The heterologous gene is more preferably derived from
Bacillus thuringiensis.
In the context of the present invention, the compound of the
formula (I) is applied to the seed. The seed is preferably treated
in a state in which it is sufficiently stable for no damage to
occur in the course of treatment. In general, the seed can be
treated at any time between harvest and sowing. It is customary to
use seed which has been separated from the plant and freed from
cobs, shells, stalks, coats, hairs or the flesh of the fruits. For
example, it is possible to use seed which has been harvested,
cleaned and dried down to a moisture content which allows storage.
Alternatively, it is also possible to use seed which, after drying,
has been treated with, for example, water and then dried again, for
example priming. In the case of rice seed, it is also possible to
use seed which, for example, has been pre-swollen in water up to a
particular stage (pigeon breast stage), which leads to better
germination and to more homogeneous emergence.
When treating the seed, care must generally be taken that the
amount of the compound of the formula (I) applied to the seed
and/or the amount of further additives is chosen in such a way that
the germination of the seed is not adversely affected, or that the
resulting plant is not damaged. This has to be ensured particularly
in the case of active ingredients which can exhibit phytotoxic
effects at certain application rates.
In general, the compounds of the formula (I) are applied to the
seed in the form of a suitable formulation. Suitable formulations
and processes for seed treatment are known to the person skilled in
the art.
The compounds of the formula (I) can be converted to the customary
seed dressing formulations, such as solutions, emulsions,
suspensions, powders, foams, slurries or other coating compositions
for seed, and also ULV formulations.
These formulations are produced in a known manner, by mixing the
compounds of the formula (I) with customary additives, for example
customary extenders and solvents or diluents, dyes, wetters,
dispersants, emulsifiers, antifoams, preservatives, secondary
thickeners, stickers, gibberellins and also water.
Useful dyes which may be present in the seed dressing formulations
usable in accordance with the invention are all dyes which are
customary for such purposes. It is possible to use either pigments,
which are sparingly soluble in water, or dyes, which are soluble in
water. Examples include the dyes known by the names Rhodamine B,
C.I. Pigment Red 112 and C.I. Solvent Red 1.
Useful wetting agents which may be present in the seed dressing
formulations usable in accordance with the invention are all
substances which promote wetting and which are customary for the
formulation of active agrochemical ingredients. Preference is given
to using alkyl naphthalenesulphonates, such as diisopropyl or
diisobutyl naphthalenesulphonates.
Suitable dispersants and/or emulsifiers which may be present in the
seed dressing formulations usable in accordance with the invention
are all nonionic, anionic and cationic dispersants customary for
the formulation of active agrochemical compounds. Preference is
given to using nonionic or anionic dispersants or mixtures of
nonionic or anionic dispersants. Suitable nonionic dispersants
include in particular ethylene oxide/propylene oxide block
polymers, alkylphenol polyglycol ethers and tristryrylphenol
polyglycol ethers, and the phosphated or sulphated derivatives
thereof. Suitable anionic dispersants are especially
lignosulphonates, polyacrylic acid salts and
arylsulphonate/formaldehyde condensates.
Antifoams which may be present in the seed dressing formulations
usable in accordance with the invention are all foam-inhibiting
substances conventionally used for formulation of active
agrochemical ingredients. Silicone antifoams and magnesium stearate
can be used with preference.
Preservatives which may be present in the seed dressing
formulations usable in accordance with the invention are all
substances usable for such purposes in agrochemical compositions.
Examples include dichlorophene and benzyl alcohol hemiformal.
Secondary thickeners which may be present in the seed dressing
formulations usable in accordance with the invention are all
substances which can be used for such purposes in agrochemical
compositions. Preferred examples include cellulose derivatives,
acrylic acid derivatives, xanthan, modified clays and finely
divided silica.
Useful stickers which may be present in the seed dressing
formulations usable in accordance with the invention are all
customary binders usable in seed dressing products. Preferred
examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl
alcohol and tylose.
Gibberellins which may be present in the seed dressing formulations
usable in accordance with the invention are preferably the
gibberellins A1, A3 (=gibberellic acid), A4 and A7; particular
preference is given to using gibberellic acid. The gibberellins are
known (cf. R. Wegler "Chemie der Pflanzenschutz-und
Schadlingsbekaimpfungsmittel", vol. 2, Springer Verlag, 1970, pp.
401-412).
The seed dressing formulations usable in accordance with the
invention can be used to treat a wide variety of different kinds of
seed, either directly or after prior dilution with water. For
instance, the concentrates or the preparations obtainable therefrom
by dilution with water can be used to dress the seed of cereals,
such as wheat, barley, rye, oats, and triticale, and also the seed
of maize, rice, oilseed rape, peas, beans, cotton, sunflowers, soya
beans and beets, or else a wide variety of different vegetable
seed. The seed dressing formulations usable in accordance with the
invention, or the dilute use forms thereof, can also be used to
dress seed of transgenic plants.
For treatment of seed with the seed dressing formulations usable in
accordance with the invention, or the use forms prepared therefrom,
all mixing units usable customarily for the seed dressing are
useful. Specifically, the procedure in seed dressing is to place
the seed into a mixer in batchwise or continuous operation, to add
the particular desired amount of seed dressing formulations, either
as such or after prior dilution with water, and to mix until the
formulation is distributed homogeneously on the seed. If
appropriate, this is followed by a drying operation.
The application rate of the seed dressing formulations usable in
accordance with the invention can be varied within a relatively
wide range. It is guided by the particular content of the compounds
of the formula (I) in the formulations and by the seed. The
application rates of the compound of the formula (I) are generally
between 0.001 and 50 g per kilogram of seed, preferably between
0.01 and 15 g per kilogram of seed.
Animal Health
In the animal health field, i.e. the field of veterinary medicine,
the compounds of the formula (I) are active against animal
parasites, in particular ectoparasites or endoparasites. The term
"endoparasites" includes especially helminths and protozoa, such as
coccidia. Ectoparasites are typically and preferably arthropods,
especially insects and acarids.
In the field of veterinary medicine, the compounds of the formula
(I) having favourable homeotherm toxicity are suitable for
controlling parasites which occur in animal breeding and animal
husbandry in livestock, breeding animals, zoo animals, laboratory
animals, experimental animals and domestic animals. They are active
against all or specific stages of development of the parasites.
Agricultural livestock include, for example, mammals such as sheep,
goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow
deer, and particularly cattle and pigs; poultry such as turkeys,
ducks, geese, and particularly chickens; fish and crustaceans, for
example in aquaculture, and also insects such as bees.
Domestic animals include, for example, mammals, such as hamsters,
guinea pigs, rats, mice, chinchillas, ferrets, and particularly
dogs, cats, caged birds, reptiles, amphibians and aquarium
fish.
In a preferred embodiment, the compounds of the formula (I) are
administered to mammals.
In another preferred embodiment, the compounds of the formula (I)
are administered to birds, namely caged birds and particularly
poultry.
Use of the compounds of the formula (I) for the control of animal
parasites is intended to reduce or prevent illness, cases of death
and reductions in performance (in the case of meat, milk, wool,
hides, eggs, honey and the like), such that more economical and
simpler animal keeping is enabled and better animal well-being is
achievable.
In relation to the animal health field, the term "control" or
"controlling" means that the compounds of the formula (I) are
effective in reducing the incidence of the particular parasite in
an animal infected with such parasites to an innocuous degree. More
specifically, "controlling" in the present context means that the
compound of the formula (I) can kill the respective parasite,
inhibit its growth, or inhibit its proliferation.
Arthropods Include:
from the order of the Anoplurida, for example Haematopinus spp.,
Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.;
from the order of the Mallophagida and the suborders Amblycerina
and Ischnocerina, for example Trimenopon spp., Menopon spp.,
Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp.,
Damalina spp., Trichodectes spp., Felicola spp.; from the order of
the Diptera and the suborders Nematocerina and Brachycerina, for
example Aedes spp., Anopheles spp., Culex spp., Simulium spp.,
Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,
Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp.,
Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp.,
Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia
spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp.,
Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp.,
Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp.,
Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.;
from the order of the Siphonapterida, for example Pulex spp.,
Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus
spp.;
from the order of the Heteropterida, for example Cimex spp.,
Triatoma spp., Rhodnius spp., Panstrongylus spp.; and also nuisance
and hygiene pests from the order of the Blattarida.
Arthropods Further Include:
from the subclass of the Acari (Acarina) and the order of the
Metastigmata, for example from the family of Argasidae like Argas
spp., Ornithodorus spp., Otobius spp., from the family of Ixodidae
like Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp.,
Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus
spp. (the original genus of multi-host ticks); from the order of
Mesostigmata like Dermanyssus spp., Omithonyssus spp., Pneumonyssus
spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa
spp., Acarapis spp.; from the order of the Actinedida
(Prostigmata), for example Acarapis spp., Cheyletiella spp.,
Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,
Trombicula spp., Neotrombiculla spp., Listrophorus spp.; and from
the order of the Acaridida (Astigmata), for example Acarus spp.,
Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus
spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes
spp., Notoedres spp., Knemidocoptes spp., Cytodites spp.,
Laminosioptes spp.
Parasitic Protozoa Include:
Mastigophora (Flagellata), for example Trypanosomatidae, for
example, Trypanosoma b. brucei, T. b. gambiense, T. b. rhodesiense,
T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T.
percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani,
L. tropica, for example Trichomonadidae, for example, Giardia
lamblia, G. canis;
Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example,
Entamoeba histolytica, Hartmanellidae, for example, Acanthamoeba
sp., Harmanella sp.;
Apicomplexa (Sporozoa) such as Eimeridae, for example, Eimeria
acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina,
E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E.
canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E.
crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E.
falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani,
E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E.
leucarti, E. magna, E. maxima, E. media, E. meleagridis, E.
meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E.
ovis, E. parva, E. pavonis, E. perforans, E. phasani, E.
piriformis, E. praecox, E. residua, E. scabra, E. spec., E.
stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuemii,
Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis,
I. rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium
spec., in particular C. parvum; such as Toxoplasmadidae, for
example, Toxoplasma gondii, Hammondia heydornii, Neospora caninum,
Besnoitia besnoitii; such as
Sarcocystidae, for example, Sarcocystis bovicanis, S. bovihominis,
S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such
as Leucozoidae, for example, Leucozytozoon simondi, such as
Plasmodiidae, for example, Plasmodium berghei, P. falciparum, P.
malariae, P. ovale, P. vivax, P. spec., such as Piroplasmea, for
example, Babesia argentina, B. bovis, B. canis, B. spec., Theileria
parva, Theileria spec., such as Adeleina, for example, Hepatozoon
canis, H. spec.
Pathogenic endoparasites, which are helminths, include
Platyhelmintha (e.g. Monogenea, cestodes and trematodes),
roundworms, Acanthocephala, and Pentastoma. These include:
Monogenea: for example: Gyrodactylus spp., Dactylogyrus spp.,
Polystoma spp.
Cestodes: from the order of the Pseudophyllidea, for example:
Diphyllobothrium spp., Spirometra spp., Schistocephalus spp.,
Ligula spp., Bothridium spp., Diphlogonoporus spp.;
from the order of the Cyclophyllida, for example: Mesocestoides
spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp.,
Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp.,
Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp.,
Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina
spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp.,
Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium
spp.;
Trematodes: from the class of the Digenea, for example: Diplostomum
spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia
spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia
spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp.,
Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp.,
Fasciola spp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum
spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp.,
Cotylophoron spp., Gigantocotyle spp., Fischoederius spp.,
Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis
spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp.,
Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus
spp., Opisthorchis spp., Clonorchis spp., Metorchis spp.,
Heterophyes spp., Metagonimus spp.; nematodes: Trichinellida, for
example: Trichuris spp., Capillaria spp., Paracapillaria spp.,
Eucoleus spp., Trichomosoides spp., Trichinella spp.;
from the order of the Tylenchida, for example: Micronema spp.,
Strongyloides spp.;
from the order of the Rhabditida, for example: Strongylus spp.,
Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,
Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,
Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,
Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,
Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,
Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp.,
Muellerius spp., Protostrongylus spp., Neostrongylus spp.,
Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp.,
Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp.,
Paracrenosoma spp., Oslerus spp., Angiostrongylus spp.,
Aelurostrongylus spp., Filaroides spp., Parafilaroides spp.,
Trichostrongylus spp., Haemonchus spp., Ostertagia spp.,
Teladorsagia spp., Marshallagia spp., Cooperia spp.,
Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,
Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus
spp.;
from the order of the Spirurida, for example: Oxyuris spp.,
Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp.,
Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp.,
Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.;
Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema
spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus
spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa
spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria
spp., Onchocerca spp., Spirocerca spp.;
Acanthocephala: from the order of the Oligacanthorhynchida, for
example: Macracanthorhynchus spp., Prosthenorchis spp.; from the
order of the Polymorphida, for example: Filicollis spp.; from the
order of the Moniliformida, for example: Moniliformis spp.;
from the order of the Echinorhynchida, for example, Acanthocephalus
spp., Echinorhynchus spp., Leptorhynchoides spp.;
Pentastoma: from the order of the Porocephalida, for example,
Linguatula spp.
In the veterinary field and in animal keeping, the compounds of the
formula (I) are administered by methods generally known in the art,
such as via the enteral, parenteral, dermal or nasal route in the
form of suitable preparations. Administration may be prophylactic
or therapeutic.
Thus, one embodiment of the present invention refers to the use of
a compound of the formula (I) as medicament.
A further aspect refers to the use of a compound of the formula (I)
as an antiendoparasitic agent, in particular as a helminthicidal
agent or antiprotozoic agent. Compounds of the formula (I) are
suitable for use as an antiendoparasitic agent, especially as a
helminthicidal agent or antiprotozoic agent, for example in animal
husbandry, in animal breeding, in buildings for livestock and in
the hygiene sector.
A further aspect in turn relates to the use of a compound of the
formula (I) as an antiectoparasitic agent, especially an
arthropodicide such as an insecticide or an acaricide. A further
aspect relates to the use of a compound of the formula (I) as an
antiectoparasitic agent, especially an arthropodicide such as an
insecticide or an acaricide, for example in animal husbandry, in
animal breeding, in buildings for livestock or in the hygiene
sector.
Vector Control
The compounds of the formula (I) can also be used in vector
control. In the context of the present invention, a vector is an
arthropod, especially an insect or arachnid, capable of
transmitting pathogens, for example, viruses, worms, single-cell
organisms and bacteria, from a reservoir (plant, animal, human,
etc.) to a host. The pathogens can be transmitted either
mechanically (for example trachoma by non-stinging flies) to a host
or after injection (for example malaria parasites by mosquitoes)
into a host.
Examples of vectors and the diseases or pathogens they transmit
are: 1) Mosquitoes Anopheles: malaria, filariasis; Culex: Japanese
encephalitis, filariasis, other viral diseases, transmission of
worms; Aedes: yellow fever, dengue fever, filariasis, other viral
diseases; Simuliidae: transmission of worms, in particular
Onchocerca volvulus; 2) Lice: skin infections, epidemic typhus; 3)
Fleas: plague, endemic typhus; 4) Flies: sleeping sickness
(trypanosomiasis); cholera, other bacterial diseases; 5) Mites:
acariosis, epidemic typhus, rickettsialpox, tularaemia, Saint Louis
encephalitis, tick-borne encephalitis (TBE), Crimean-Congo
haemorrhagic fever, borreliosis; 6) Ticks: borellioses such as
Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella
burnetii), babesioses (Babesia canis canis).
Examples of vectors in the context of the present invention are
insects, for example aphids, flies, leafhoppers or thrips, which
can transmit plant viruses to plants. Other vectors capable of
transmitting plant viruses are spider mites, lice, beetles and
nematodes.
Further examples of vectors in the context of the present invention
are insects and arachnids such as mosquitoes, especially of the
genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A.
funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites
and ticks, which can transmit pathogens to animals and/or
humans.
Vector control is also possible if the compounds of the formula (I)
are resistance-breaking.
Compounds of the formula (I) are suitable for use in the prevention
of diseases and/or pathogens transmitted by vectors. Thus, a
further aspect of the present invention is the use of compounds of
the formula (I) for vector control, for example in agriculture, in
horticulture, in forestry, in gardens and in leisure facilities,
and also in the protection of materials and stored products.
Protection of Industrial Materials
The compounds of the formula (I) are suitable for protecting
industrial materials against attack or destruction by insects, for
example from the orders Coleoptera, Hymenoptera, Isoptera,
Lepidoptera, Psocoptera and Zygentoma.
Industrial materials in the present context are understood to mean
inanimate materials, such as preferably plastics, adhesives, sizes,
papers and cards, leather, wood, processed wood products and
coating compositions. The use of the invention for protection of
wood is particularly preferred.
In a further embodiment, the compounds of the formula (I) are used
together with at least one further insecticide and/or at least one
fungicide.
In a further embodiment, the compounds of the formula (I) are
present as a ready-to-use pesticide, i.e. they can be applied to
the material in question without further modifications. Suitable
further insecticides or fungicides are in particular those
mentioned above.
Surprisingly, it has also been found that the compounds of the
formula (I) can be employed for protecting objects which come into
contact with saltwater or brackish water, in particular hulls,
screens, nets, buildings, moorings and signalling systems, against
fouling. It is equally possible to use the compounds of the formula
(I), alone or in combinations with other active ingredients, as
antifouling agents.
Control of Animal Pests in the Hygiene Sector
The compounds of the formula (I) are suitable for controlling
animal pests in the hygiene sector. More particularly, the
invention can be used in the domestic sector, in the hygiene sector
and in the protection of stored products, particularly for control
of insects, arachnids and mites encountered in enclosed spaces, for
example dwellings, factory halls, offices, vehicle cabins. For
controlling animal pests, the compounds of the formula (I) are used
alone or in combination with other active ingredients and/or
auxiliaries. They are preferably used in domestic insecticide
products. The compounds of the formula (I) are effective against
sensitive and resistant species, and against all developmental
stages.
These pests include, for example, pests from the class Arachnida,
from the orders Scorpiones, Araneae and Opiliones, from the classes
Chilopoda and Diplopoda, from the class Insecta the order
Blattodea, from the orders Coleoptera, Dermaptera, Diptera,
Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera,
Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma
and from the class Malacostraca the order Isopoda.
Application is effected, for example, in aerosols, unpressurized
spray products, for example pump and atomizer sprays, automatic
fogging systems, foggers, foams, gels, evaporator products with
evaporator tablets made of cellulose or plastic, liquid
evaporators, gel and membrane evaporators, propeller-driven
evaporators, energy-free, or passive, evaporation systems, moth
papers, moth bags and moth gels, as granules or dusts, in baits for
spreading or bait stations.
PREPARATION EXAMPLES
Preparation Example 1
3-Methyl-2-[3-(methylsulphonyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(triflu-
oromethyl)-3H-imidazo[4,5-c]pyridine (I-36)
##STR00045##
41 mg (0.10 mmol) of
3-methyl-2-[3-(methylsulphanyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifl-
uoromethyl)-3H-imidazo[4,5-c]pyridine are dissolved in 4 ml of
dichloromethane, 86.5 mg (0.36 mmol) of meta-chloroperbenzoic acid
are added at 0.degree. C. and then the mixture is stirred at room
temperature for 20 h. The mixture is admixed with sodium bisulphite
solution, stirred for 10 min, diluted with 30 ml of water and
adjusted to pH 9-10 with 45% sodium hydroxide solution. The mixture
is extracted three times with dichloromethane and then the combined
organic phases are freed of the solvent under reduced pressure.
(log P (neutral): 2.64; MH.sup.+: 425; .sup.1H NMR (400 MHz,
D.sub.6-DMSO) .delta. ppm: 3.70 (s, 3H), 3.93 (s, 3H), 8.35 (s,
1H), 8.83 (s, 1H), 9.32 (s, 1H), 9.58 (s, 1H).
Preparation of
3-methyl-2-[3-(methylsulphinyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifl-
uoro-methyl)-3H-imidazo[4,5-c]pyridine (I-26)
##STR00046##
41 mg (0.10 mmol) of
3-methyl-2-[3-(methylsulphanyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifl-
uoromethyl)-3H-imidazo[4,5-c]pyridine are dissolved in 4 ml of
dichloromethane, and 1.92 mg (0.04 mmol) of formic acid and 28.44
mg of a 35% hydrogen peroxide solution are added at room
temperature. The mixture is stirred at room temperature for 5 h,
sodium bisulphite solution is added and the mixture is stirred for
a further 3 h. Subsequently, the mixture is stirred with 10% sodium
hydrogencarbonate solution, the organic phase is removed, the
aqueous phase is extracted twice with dichloromethane, and the
organic phases are combined and then freed of the solvent under
reduced pressure.
(log P (neutral): 2.76; MH.sup.+: 409; .sup.1H NMR (400 MHz,
D.sub.6-DMSO) .delta. ppm: 3.15 (s, 3H), 4.35 (s, 3H), 8.37 (s,
1H), 8.85 (s, 1H), 9.37 (s, 1H), 9.39 (s, 1H).
Preparation of
3-methyl-2-[3-(methylsulphanyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifl-
uoromethyl)-3H-imidazo[4,5-c]pyridine (I-3)
##STR00047##
150 mg (0.39 mmol) of
2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-
-3H-imidazo[4,5-c]pyridine and 83 mg (1.18 mmol) of sodium
methanethiolate are stirred in DMF at room temperature for 6 h. The
mixture is admixed with water and extracted three times with ethyl
acetate. The combined organic phases are washed with a sodium
chloride solution, removed, dried over sodium sulphate and freed of
the solvent under reduced pressure.
(log P (neutral): 3.16; MH.sup.+: 393; .sup.1H NMR (400 MHz,
D.sub.6-DMSO) .delta. ppm: 2.58 (s, 3H), 4.06 (s, 3H), 8.27 (s,
1H), 8.32 (s, 1H), 8.95 (s, 1H), 9.29 (s, 1H).
Preparation of
2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-
-3H-imidazo[4,5-c]pyridine (IX-01)
##STR00048##
950 mg (4.97 mmol) of
N.sup.3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (II-01),
1.12 g (4.97 mmol) of
3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid and 953 mg
(4.97 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide
hydrochloride (EDCI) are stirred in 10 ml of pyridine at
115.degree. C. for 7 h. The reaction mixture is freed of solvent
under reduced pressure, then water is added and the mixture is
extracted three times with ethyl acetate. The combined organic
phases are dried over sodium sulphate, concentrated again and
purified by column chromatography purification by means of
preparative HPLC with a water/acetonitrile gradient as eluent.
(log P (neutral): 2.96; MH.sup.+: 381; .sup.1H NMR (400 MHz,
D.sub.6-DMSO) .delta. ppm: 4.00 (s, 3H), 8.35 (s, 1H), 8.86 (s,
1H), 9.22 (s, 1H), 9.30 (s, 1H).
Preparation of
3-chloro-N-[5-(methylamino)-2-(trifluoromethyl)pyridin-4-yl]-5-(trifluoro-
methyl)pyridine-2-carboxamide (VIII-01)
By the above method for preparation of
2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-
-3H-imidazo[4,5-c]pyridine (IX-01) from
N.sup.3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (II-01) and
3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, it is
likewise possible to prepare the compound
3-chloro-N-[5-(methylamino)-2-(trifluoromethyl)pyridin-4-yl]-5-(trifluoro-
methyl)pyridine-2-carboxamide (VIII-01) as an intermediate for the
compound (IX-01).
##STR00049##
(log P (neutral): 3.09; MH.sup.+: 399; .sup.1H NMR (400 MHz,
D.sub.6-DMSO) .delta. ppm: 2.87 (d, 3H), 5.97 (q, 1H), 8.10 (s,
1H), 8.18 (s, 1H), 8.73 (s, 1H), 9.09 (s, 1H), 10.40 (br. S,
1H).
Preparation of
N.sup.3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (II-01)
##STR00050##
A solution of 0.93 g (3.0 mmol) of benzyl
[4-amino-6-(trifluoromethyl)pyridin-3-yl]carbamate in 85 ml of
tetrahydrofuran is cooled to 0.degree. C. and admixed with 0.65 g
(17 mmol) of lithium aluminium hydride. The mixture is stirred
under argon at 0.degree. C. for 15 min and then at room temperature
for 4 h. The excess of lithium aluminium hydride is destroyed by
the addition of ethyl acetate, the mixture is filtered and the
filtrate is extracted twice with 50 ml each time of 2 N
hydrochloric acid. The combined hydrochloric acid extracts are
adjusted to pH=8 with sodium carbonate while cooling. Subsequently,
the mixture is extracted twice with 100 ml each time of ethyl
acetate, the organic phases are combined and dried with sodium
sulphate, and the solvent is distilled off under reduced pressure.
The product is purified further by recrystallization from a mixture
of hexane/isopropanol.
(MH.sup.+: 192; .sup.1H NMR (400 MHz, D.sub.6-DMSO) .delta. ppm:
2.81 (d, 3H), 5.22 (q, 1H), 5.82 (br. s, 2H), 6.84 (s, 1H), 7.57
(s, 1H).
Preparation of benzyl
[4-amino-6-(trifluoromethyl)pyridin-3-yl]carbamate
##STR00051##
0.91 g of 6-(trifluoromethyl)pyridine-3,4-diamine is dissolved in a
mixture of 20 ml of tetrahydrofuran and 2 ml of pyridine. A
solution of 1.07 g (6.3 mmol) of benzyl chlorocarbonate (benzyl
chloroformate) in 2 ml of tetrahydrofuran is added dropwise while
stirring. Subsequently, the reaction mixture is stirred overnight,
diluted with 100 ml of water and extracted twice with 100 ml each
time of ethyl acetate. The combined organic phases are washed with
50 ml of water, dried over sodium sulphate and concentrated.
By washing the residue with 50 ml of chloroform, the product is
obtained in the form of a white solid.
(.sup.1H NMR (500 MHz, D.sub.6-DMSO) .delta. ppm: 5.15 (s, 2H),
6.40 (br. s 2H), 7.05 (s, 1H), 7.30-7.45 (m, 5H), 8.35 (s, 1H),
9.00 (br. s, 1H).
Preparation Example 2
2-[2-(Ethylsulphanyl)phenyl]-6-(trifluoromethyl)[1,3]oxazolo[5,4-c]pyridin-
e (I-35)
##STR00052##
400 mg (1.16 mmol) of
2-(ethylsulphanyl)-N-[5-hydroxy-2-(trifluoromethyl)pyridin-4-yl]benzamide
and 398 mg (1.51 mmol) of triphenylphosphine are dissolved in 12 ml
of THF, and 661 mg (1.51 mmol) of 40% diethyl azodicarboxylate
(DEAD) in toluene are added dropwise at RT. The mixture is stirred
at room temperature for 3 h. Subsequently, the solvent is distilled
off under reduced pressure and the residue is purified by column
chromatography purification with a water/acetonitrile gradient as
eluent.
(log P (neutral): 4.07; MH.sup.+: 325; .sup.1H NMR (400 MHz,
D.sub.6-DMSO) .delta. ppm: 1.32 (t, 3H), 3.10 (q, 2H), 7.42 (t,
1H), 7.60-7.69 (m, 2H), 8.21 (d, 1H), 8.54 (s, 1H), 9.33 (s,
1H).
Preparation of
2-(ethylsulphanyl)-N-[5-hydroxy-2-(trifluoromethyl)pyridin-4-yl]benzamide
(VIII-02)
##STR00053##
206 mg (1.12 mmol) of 2-(ethylsulphanyl)benzoic acid and 201 mg
(1.12 mmol) of 4-amino-6-(trifluoromethyl)pyridin-3-ol are
dissolved in 5 ml of pyridine, 325 mg (1.69 mmol) of
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI)
are added and the mixture is stirred at 50.degree. C. for 2 h and
at 80.degree. C. for 3 h. The solvent is distilled off under
reduced pressure, and the residue is taken up in water and
extracted with ethyl acetate. The organic phase is washed with a
sodium chloride solution, removed, dried over sodium sulphate and
concentrated. The residue is purified by column chromatography
purification by means of preparative HPLC with a water/acetonitrile
gradient as eluent.
(log P (neutral): 1.59; MH.sup.+: 343; .sup.1H NMR (400 MHz,
D.sub.6-DMSO) .delta. ppm: 1.21 (t, 3H), 2.98 (q, 2H), 7.29-7.34
(m, 1H), 7.48-7.53 (m, 2H), 7.61 (d, 1H), 8.29 (s, 1H), 8.55 (s,
1H), 9.99 (s, 1H), 11.31 (br. S, 1H).
Preparation of 4-amino-6-(trifluoromethyl)pyridin-3-ol (II-02)
##STR00054##
12.3 g (42.1 mmol) of tert-butyl
[5-methoxy-2-(trifluoromethyl)pyridin-4-yl]carbamate are dissolved
in 300 ml of dichloromethane and cooled to -78.degree. C., and 42.2
g (168 mmol) of boron tribromide in 150 ml of dichloromethane are
added dropwise at this temperature. The mixture is allowed to come
to room temperature overnight, then 400 ml of sodium
hydrogencarbonate solution are added and the mixture is extracted
three times with 100 ml each time of dichloromethane. The solvent
is distilled off and the residue is purified by chromatography on
silica gel.
(.sup.1H NMR (90 MHz, D.sub.6-DMSO) .delta. ppm: 7.00 (s, 1H), 7.9
(s, 1H).
Preparation of tert-butyl
[5-methoxy-2-(trifluoromethyl)pyridin-4-yl]carbamate
##STR00055##
To a solution of 9.80 g (44.3 mmol) of
5-methoxy-2-(trifluoromethyl)isonicotinic acid in 980 ml of
tert-butanol are added, at room temperature, 65 g of 4 A molecular
sieve, 14.6 g (53.1 mmol) of diphenylphosphoryl azide (DPPA) and
5.37 g (53.1 mmol) of triethylamine. The reaction mixture is
stirred at 81.degree. C. for 23 h and then the 4 A molecular sieve
is filtered off. After the tert-butanol has been distilled off
under reduced pressure, the residue is admixed with 500 ml of ethyl
acetate, washed with 250 ml of 2 N hydrochloric acid, 250 ml of
saturated aqueous sodium hydrogencarbonate solution, 250 ml of
water and 250 ml of sodium chloride solution, and dried over sodium
sulphate. The solvent is removed under reduced pressure and the
residue is washed three times with 15 ml each time of ethyl acetate
and dried under reduced pressure. The ethyl acetate phase is
purified by chromatography on silica gel (hexane/EtOAc
4:1=>2:1).
(.sup.1H NMR (90 MHz, CDCl.sub.3) .delta. ppm: 1.5 (s, 9H), 4.0 (s,
3H), 8.2 (s, 1H), 8.5 (s, 1H).
Preparation of
2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluo-
romethyl)-phenyl]imidazo[4,5-c]pyridine (I-64)
##STR00056##
A solution of 62 mg (0.58 mmol) of sodium carbonate in 2 ml of a
4:1 mixture of 1,2-dimethoxyethane and water is degassed in an
ultrasound bath, and 73 mg (0.19 mmol) of
6-chloro-2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methylimida-
zo[4,5-c]pyridine and 67 mg (0.35 mmol) of
[4-(trifluoromethyl)phenyl]boronic acid are added. The vessel is
flooded with argon and then 23 mg (20 .mu.mol) of
tetrakis(triphenylphosphine)palladium are added. The mixture is
heated in a CEM Discover microwave to 140.degree. C. for 2 h 10
min, then admixed with a further 68 mg (59 .mu.mol) of
tetrakis(triphenylphosphine)palladium and heated to 140.degree. C.
for a further 4 h. The reaction mixture is filtered through a
Celite bed which has been rinsed with ethyl acetate. After the
solvent has been removed under reduced pressure, the residue is
separated chromatographically by MPLC on silica gel (gradient:
ethyl acetate/cyclohexane). This is followed by another
chromatographic separation by means of preparative HPLC (gradient:
H.sub.2O/acetonitrile). In this way, 14 mg (99% purity, 15% yield)
of
2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluo-
romethyl)phenyl]imidazo[4,5-c]pyridine are obtained.
(log P (neutral): 3.95; MH.sup.+: 483; .sup.1H NMR (400 MHz,
D.sub.6-DMSO) .delta. ppm: 9.275 (2.6); 9.271 (2.5); 8.943 (4.3);
8.584 (2.6); 8.580 (2.6); 8.318 (0.5); 7.701 (3.0); 7.680 (3.9);
7.548 (3.8); 7.527 (3.0); 7.410 (4.6); 3.890 (16.0); 3.329 (75.4);
3.140 (1.3); 3.122 (4.2); 3.104 (4.3); 3.086 (1.4); 2.676 (0.9);
2.671 (1.2); 2.667 (0.9); 2.507 (140.3); 2.502 (179.9); 2.498
(134.5); 2.334 (0.9); 2.329 (1.2); 2.325 (0.9); 1.281 (4.6); 1.263
(9.7); 1.245 (4.5); 0.146 (0.4); 0.008 (3.6); 0.000 (84.0); -0.150
(0.4).
Preparation of
2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluo-
romethyl)-imidazol-1-yl]imidazo[4,5-c]pyridine (I-74)
##STR00057##
Under argon, 99 mg (0.27 mmol) of
6-chloro-2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methylimida-
zo[4,5-c]pyridine, 23 .mu.l (0.15 mmol) of
trans-N,N'-dimethylcyclohexane-1,2-diamine, 6.8 mg (36 .mu.mol) of
copper(I) iodide, 30 mg (0.22 mmol) of
4-(trifluoromethyl)-1H-imidazole and 64 mg (0.46 mmol) of potassium
carbonate are added to 1 ml of degassed toluene. The vessel is
closed and the reaction mixture is heated in a CEM Discover
microwave reactor to 110.degree. C. for 4 h. After cooling to room
temperature, ethyl acetate is added and the mixture is filtered
through a Celite bed, which is subsequently rinsed with ethyl
acetate. The solvent is removed under reduced pressure and the
residue is separated chromatographically by MPLC on silica gel
(gradient: ethyl acetate/cyclohexane). In this way, 22 mg (100%
purity, 18% yield) of
2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluo-
romethyl)imidazol-1-yl]imidazo[4,5-c]pyridine are obtained.
(log P (neutral): 3.36; MH.sup.+: 473; .sup.1H NMR (600 MHz,
CD.sub.3CN) .delta. ppm: 8.905 (3.0); 8.903 (3.0); 8.852 (1.6);
8.850 (1.6); 8.500 (1.9); 8.313 (1.5); 8.311 (2.1); 8.309 (1.4);
8.183 (1.7); 8.181 (1.7); 7.962 (3.4); 7.961 (3.4); 4.001 (16.0);
3.940 (0.4); 3.124 (1.1); 3.111 (3.4); 3.099 (3.5); 3.087 (1.2);
2.639 (0.7); 2.184 (55.7); 2.109 (1.2); 2.005 (2.2); 1.998 (195.7);
1.989 (2.7); 1.985 (1.8); 1.981 (10.0); 1.977 (18.2); 1.973 (26.5);
1.969 (18.0); 1.965 (9.0); 1.882 (1.2); 1.419 (0.4); 1.404 (0.7);
1.373 (0.6); 1.330 (4.1); 1.318 (9.0); 1.309 (1.6); 1.305 (5.2);
1.301 (3.4); 0.914 (0.6).
In analogy to the examples and according to the above-described
preparation processes, the following compounds of the formula (I)
can be obtained:
##STR00058## where A.sup.3 is oxygen and the other substituents are
each as defined in the following table:
TABLE-US-00001 Ex. R.sup.1 N A.sup.4 A.sup.5 R.sup.3 A.sup.2
A.sup.1 R.sup.2a R.sup.2b I-1 CH.sub.3 0 N CH CF.sub.3 O CH Cl H
I-2 C.sub.2H.sub.5 0 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-3
CH.sub.3 0 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-4 CH.sub.3 0 CH
CH CF.sub.3 N-methyl CH F H I-5 CH.sub.3 0 CH CH CF.sub.3 N-methyl
CH CF.sub.3 H I-6 CH.sub.3 0 N CH CF.sub.3 N-methyl CH Cl H I-7
--(CH.sub.2).sub.2--SO.sub.2--C.sub.2H.sub.5 2 CH CH CF.sub.3
N-methyl- N CF.sub.3 H I-8 i-C.sub.3H.sub.7 1 CH CH CF.sub.3
N-methyl N CF.sub.3 H I-9 C.sub.2H.sub.5 0 N CH CF.sub.3 O CH H H
I-10 CH.sub.3 1 CH CH CF.sub.3 N-methyl CH Cl H I-11 CH.sub.3 2 CH
CH CF.sub.3 N-methyl CH Cl H I-12 CH.sub.3 1 CH CH CF.sub.3
N-methyl CH F H I-13 C.sub.2H.sub.5 1 CH CH CF.sub.3 N-methyl CH H
5-Cl* I-14 CH.sub.3 2 CH CH CF.sub.3 N-methyl CH 3 H I-15
C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl N H H I-16
i-C.sub.3H.sub.7 2 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-17
C.sub.2H.sub.5 0 CH CH CF.sub.3 N-methyl CH H H I-18 C.sub.2H.sub.5
2 CH CH CF.sub.3 N-methyl CH H H I-19 C.sub.2H.sub.5 0 CH CH
CF.sub.3 N-methyl CH H 5-Cl* I-20 CH.sub.3 2 CH CH CF.sub.3
N-methyl CH F H I-21 C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl N
CF.sub.3 H I-22 C.sub.2H.sub.5 1 CH CH CF.sub.3 N-methyl CH H H
I-23 --(CH.sub.2).sub.2--S--C.sub.2H.sub.5 0 CH CH CF.sub.3
N-methyl N CF.- sub.3 H I-24 C.sub.2H.sub.5 0 CH CH CF.sub.3
N-methyl N H H I-25 CH.sub.3 0 CH CH CF.sub.3 N-methyl CH Cl H I-26
CH.sub.3 1 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-27 oxetan-3-yl 2
CH CH CF.sub.3 N-methyl CH H H I-28 C.sub.2H.sub.5 0 N CH CF.sub.3
N-methyl N CF.sub.3 H I-29 CF.sub.3 0 CH CH CF.sub.3 N-methyl N H H
I-30 CH.sub.3 1 CH CH CF.sub.3 N-methyl CH CF.sub.3 H I-31
n-C.sub.3H.sub.7 0 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-32
n-C.sub.3H.sub.7 2 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-33
C.sub.2H.sub.5 1 CH CH CF.sub.3 N-methyl N H H I-34 CH.sub.3 0 CH
CH CF.sub.3 O CH Cl H I-35 C.sub.2H.sub.5 0 CH CH CF.sub.3 O CH H H
I-36 CH.sub.3 2 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-37
C.sub.2H.sub.5 1 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-38
C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl CH H 5-Cl* I-39
n-C.sub.3H.sub.7 1 CH CH CF.sub.3 N-methyl N CF.sub.3 H I-40
oxetan-3-yl 0 CH CH CF.sub.3 O CH H H I-41 i-C.sub.3H.sub.7 0 CH CH
CF.sub.3 N-methyl N CF.sub.3 H I-42 C.sub.2H.sub.5 0 CH CH CF.sub.3
N-methyl CH Cl H I-43 C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl CH
Cl H I-44 C.sub.2H.sub.5 1 CH CH CF.sub.3 N-methyl CH Cl H I-45
C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl N H 5-OMe* I-46
C.sub.2H.sub.5 0 CH CH C.sub.2F.sub.5 N-methyl N H H I-47
C.sub.2H.sub.5 0 CH CH C.sub.2F.sub.5 N-methyl N CF.sub.3 H I-48
C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl N H 3-CF.sub.3* I-49
C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl N H 5-NHCOMe* I-50
C.sub.2H.sub.5 0 CH CH CF.sub.3 N-methyl N H 5-NHCOMe* I-51
C.sub.2H.sub.5 1 CH CH CF.sub.3 N-methyl N H 3-CF.sub.3* I-52
C.sub.2H.sub.5 2 CH CH Cl N-methyl N CF.sub.3 H I-53 C.sub.2H.sub.5
0 CH CH CF.sub.3 N-methyl N H 5-OMe* I-54 CH.sub.2--CH.sub.2F 2 CH
CH CF.sub.3 N-methyl N CF.sub.3 H I-55 C.sub.2H.sub.5 0 CH CH Cl
N-methyl N CF.sub.3 H I-56 C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl
N CONH.sub.2 H I-57 CH.sub.2--CH.sub.2F 2 CH CH CF.sub.3 N-methyl N
CF.sub.3 H I-58 CH.sub.2--CH.sub.2OH 2 CH CH CF.sub.3 N-methyl N
CF.sub.3 H I-59 CH.sub.2--CH.sub.2OH 0 CH CH CF.sub.3 N-methyl N
CF.sub.3 H I-60 C.sub.2H.sub.5 0 CH CH CF.sub.3 N-methyl N
CONH.sub.2 H I-61 C.sub.2H.sub.5 1 CH CH C.sub.2F.sub.5 N-methyl N
H H I-62 C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl CH H 3-Cl* I-63
C.sub.2H.sub.5 1 CH CH C.sub.2F.sub.5 N-methyl N CF.sub.3 H I-64
C.sub.2H.sub.5 0 CH CH 4-CF.sub.3(C.sub.6H.sub.4) N-methyl N
CF.sub.3- H I-65 C.sub.2H.sub.5 0 CH CH 4-(CF.sub.3)pyrazol-1-yl
N-methyl N CF.sub.3 H- I-66 n-C.sub.3H.sub.7 0 CH CH CF.sub.3
N-methyl N H 5-OMe* I-67 CH.sub.3 0 CH CH CF.sub.3 N-methyl N H
5-OMe* I-68 C.sub.2H.sub.5 2 CH CH C.sub.2F.sub.5 N-methyl N H H
I-69 C.sub.2H.sub.5 0 CH CH 3-(CF.sub.3)pyrazol-1-yl N-methyl N
CF.sub.3 H- I-70 C.sub.2H.sub.5 0 CH CH CF.sub.3 N-methyl N H
3-CF.sub.3* I-71 n-C.sub.3H.sub.7 2 CH CH CF.sub.3 N-methyl N H
5-OMe* I-72 C.sub.2H.sub.5 2 CH CH CF.sub.3 N-methyl N CN H I-73
CH.sub.3 2 CH CH CF.sub.3 N-methyl N H 5-OMe* I-74 C.sub.2H.sub.5 0
CH CH 4-(CF.sub.3)imidazol-1-yl N-methyl N CF.sub.3 - H I-75
C.sub.2H.sub.5 2 CH CH 4-(CF.sub.3)imidazol-1-yl N-methyl N
CF.sub.3 - H I-76 C.sub.2H.sub.5 2 CH CH 4-(CF.sub.3)pyrazol-1-yl
N-methyl N CF.sub.3 H- I-77 C.sub.2H.sub.5 2 CH CH
3-(CF.sub.3)pyrazol-1-yl N-methyl N CF.sub.3 H- *In these examples,
R.sup.2b is joined in the 3 or 5 position:
##STR00059##
The log P values are measured according to EEC Directive 79/831
Annex V.A8 by HPLC (high-performance liquid chromatography) on a
reversed-phase column (C 18). Temperature: 55.degree. C.
The LC-MS determination in the acidic range is effected at pH 2.7
using 0.1% aqueous formic acid and acetonitrile (contains 0.1%
formic acid) as eluents, linear gradient from 10% acetonitrile to
95% acetonitrile. Called log P (HCOOH) in the table.
LC-MS determination in the neutral range is effected at pH 7.8 with
0.001 molar aqueous ammonium hydrogencarbonate solution and
acetonitrile as eluents; linear gradient from 10% acetonitrile to
95% acetonitrile. Called log P (neutral) in the table.
Calibration is effected with unbranched alkan-2-ones (having 3 to
16 carbon atoms) with known log P values (log P values determined
on the basis of the retention times by linear interpolation between
two successive alkanones).
The NMR data for selected examples are listed either in
conventional form (6 values, multiplet splitting, number of
hydrogen atoms) or as NMR peak lists.
The solvent in which the NMR spectrum was recorded is reported in
each case.
NMR Peak List Method
The .sup.1H NMR data of selected examples are reported in the form
of .sup.1H NMR peak lists. For each signal peak, first the .delta.
value in ppm and then the signal intensity in round brackets are
listed. The .delta. value--signal intensity number pairs for
different signal peaks are listed with separation from one another
by semicolons.
The peak list for one example therefore takes the form of:
.delta..sub.1 (intensity.sub.1); .delta..sub.2 (intensity.sub.2); .
. . ; .delta..sub.i (intensity.sub.i); . . . ; .delta..sub.n
(intensity.sub.n)
The intensity of sharp signals correlates with the height of the
signals in a printed example of an NMR spectrum in cm and shows the
true ratios of the signal intensities. In the case of broad
signals, several peaks or the middle of the signal and the relative
intensity thereof may be shown in comparison to the most intense
signal in the spectrum.
For calibration of the chemical shift of .sup.1H NMR spectra we use
tetramethylsilane and/or the chemical shift of the solvent,
particularly in the case of spectra measured in DMSO. Therefore,
the tetramethylsilane peak may, but need not, occur in NMR peak
lists.
The lists of the .sup.1H NMR peaks are similar to the conventional
.sup.1H NMR printouts and thus usually contain all peaks listed in
a conventional NMR interpretation.
In addition, like conventional .sup.1H NMR printouts, they may show
solvent signals, signals of stereoisomers of the target compounds,
which likewise form part of the subject-matter of the invention,
and/or peaks of impurities.
In the reporting of compound signals in the delta range of solvents
and/or water, our lists of .sup.1H NMR peaks show the usual solvent
peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of
water, which usually have a high intensity on average.
The peaks of stereoisomers of the target compounds and/or peaks of
impurities usually have a lower intensity on average than the peaks
of the target compounds (for example with a purity of >90%).
Such stereoisomers and/or impurities may be typical of the
particular preparation process. Their peaks can thus help in this
case to identify reproduction of our preparation process with
reference to "by-product fingerprints".
An expert calculating the peaks of the target compounds by known
methods (MestreC, ACD simulation, but also with empirically
evaluated expected values) can, if required, isolate the peaks of
the target compounds, optionally using additional intensity
filters. This isolation would be similar to the relevant peak
picking in conventional .sup.1H NMR interpretation.
Further details of .sup.1H NMR peak lists can be found in Research
Disclosure Database Number 564025.
TABLE-US-00002 Ex. LOGP_NEUTRAL LOGP_HCOOH I-1 3.77 3.86 Example 1:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.544 (6.4); 8.335
(3.9); 8.314 (4.1); 7.568 (2.9); 7.563 (3.5); 7.534 (2.5); 7.529
(1.9); 7.513 (2.3); 7.508 (1.9); 3.323 (17.6); 2.671 (0.3); 2.631
(16.0); 2.524 (1.1); 2.511 (19.3); 2.507 (38.0); 2.502 (49.6);
2.498 (35.5); 2.493 (16.9); 2.075 (0.5); 0.008 (0.9); 0.000 (21.7);
-0.008 (0.7) I-2 3.48 3.52 Example 2: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.283 (3.7); 8.960 (2.3); 8.958 (2.3);
8.334 (2.7); 8.328 (4.1); 4.030 (16.0); 3.323 (69.7); 3.181 (1.1);
3.162 (3.6); 3.144 (3.6); 3.126 (1.1); 2.891 (1.2); 2.731 (1.0);
2.676 (0.4); 2.671 (0.6); 2.667 (0.4); 2.506 (64.4); 2.502 (83.6);
2.498 (61.3); 2.333 (0.4); 2.329 (0.5); 2.324 (0.4); 1.234 (4.1);
1.215 (8.1); 1.197 (3.8); 0.008 (0.6); 0.000 (17.0); -0.008 (0.7)
I-3 3.16 3.22 Example 3: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.290 (4.0); 8.947 (2.7); 8.316 (4.5); 8.267 (2.9); 7.953
(0.4); 4.059 (16.0); 4.019 (0.7); 3.327 (63.2); 3.036 (0.3); 2.965
(0.4); 2.892 (2.5); 2.882 (0.5); 2.870 (0.5); 2.732 (2.2); 2.673
(0.5); 2.580 (15.1); 2.507 (59.9); 2.503 (71.6); 2.499 (52.5);
2.330 (0.5); 2.078 (0.4); 1.234 (0.4); 0.000 (0.4) I-4 2.65 2.70
Example 4: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.833
(0.3); 9.210 (3.9); 8.226 (4.1); 8.082 (0.6); 7.993 (0.5); 7.608
(1.3); 7.593 (1.5); 7.587 (1.6); 7.572 (1.4); 7.411 (1.3); 7.405
(1.4); 7.386 (1.4); 7.380 (1.4); 7.244 (1.0); 7.238 (0.9); 7.222
(1.6); 7.216 (1.5); 7.201 (0.8); 7.195 (0.7); 3.785 (16.0); 3.325
(80.3); 2.875 (1.0); 2.863 (1.0); 2.671 (0.7); 2.667 (0.6); 2.506
(76.1); 2.502 (99.5); 2.498 (78.2); 2.464 (2.7); 2.329 (0.6); 2.075
(0.3); 0.000 (2.6) I-5 3.26 3.30 Example 5: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.249 (3.5); 8.267 (3.7); 7.787 (1.2);
7.778 (2.7); 7.768 (2.9); 7.749 (2.1); 7.729 (0.7); 3.807 (16.0);
3.324 (21.7); 2.671 (0.4); 2.557 (15.5); 2.524 (1.1); 2.511 (22.7);
2.507 (44.4); 2.502 (57.4); 2.498 (41.7); 2.493 (20.4); 2.329
(0.4); 0.008 (2.1); 0.000 (52.3); -0.009 (2.1) I-6 2.74 2.75
Example 6: .sup.1H-NMR (601.6 MHz, CD3CN): .delta. = 9.182 (3.5);
7.526 (1.9); 7.523 (2.0); 7.459 (1.7); 7.445 (2.7); 7.403 (1.7);
7.400 (1.6); 7.390 (1.1); 7.386 (1.0); 3.927 (0.3); 3.770 (16.0);
2.978 (0.3); 2.494 (14.5); 2.222 (0.5); 2.152 (1.6); 1.966 (0.6);
1.958 (1.5); 1.954 (1.8); 1.950 (9.9); 1.946 (17.5); 1.942 (25.9);
1.938 (17.6); 1.934 (8.7); 1.387 (5.1); 1.269 (0.3); 1.212 (0.4);
0.005 (0.3); 0.000 (11.9); -0.006 (0.4) I-7 2.67 2.72 Example 7:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.411 (2.3); 9.408
(2.3); 9.379 (3.9); 9.333 (0.4); 8.751 (2.4); 8.746 (2.5); 8.460
(4.1); 8.316 (0.5); 7.903 (0.3); 4.391 (16.0); 4.199 (1.2); 4.147
(0.5); 4.138 (0.4); 4.121 (0.8); 4.114 (0.6); 4.107 (0.7); 4.100
(0.7); 4.088 (0.7); 4.068 (0.4); 3.976 (0.7); 3.854 (0.6); 3.843
(0.6); 3.833 (0.7); 3.829 (0.7); 3.819 (0.8); 3.803 (0.5); 3.795
(0.6); 3.556 (0.6); 3.543 (0.8); 3.531 (0.5); 3.523 (0.6); 3.518
(0.8); 3.510 (0.9); 3.494 (1.8); 3.477 (0.8); 3.468 (0.8); 3.464
(0.6); 3.455 (0.5); 3.443 (0.6); 3.429 (0.4); 3.325 (63.6); 3.260
(0.8); 3.257 (0.8); 3.241 (2.2); 3.238 (2.3); 3.223 (2.3); 3.219
(2.3); 3.201 (0.9); 2.676 (0.5); 2.671 (0.7); 2.667 (0.6); 2.524
(1.8); 2.511 (41.0); 2.506 (84.3); 2.502 (113.7); 2.498 (86.8);
2.493 (45.8); 2.333 (0.5); 2.329 (0.7); 2.324 (0.6); 1.252 (4.4);
1.233 (9.5); 1.214 (4.3); 0.146 (0.4); 0.008 (2.7); 0.000 (79.8);
-0.008 (4.6); -0.150 (0.4) I-8 3.46 3.54 Example 8: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.390 (2.1); 9.387 (2.1);
9.377 (3.6); 8.577 (2.1); 8.572 (2.2); 8.379 (3.7); 8.316 (0.6);
4.384 (16.0); 4.362 (0.4); 3.802 (0.3); 3.785 (0.9); 3.767 (1.3);
3.750 (0.9); 3.733 (0.4); 3.322 (86.4); 2.675 (1.0); 2.671 (1.4);
2.666 (1.0); 2.524 (3.7); 2.511 (79.1); 2.506 (160.9); 2.502
(213.1); 2.497 (155.9); 2.493 (76.9); 2.333 (1.0); 2.329 (1.4);
2.324 (1.0); 1.569 (6.3); 1.551 (6.2); 0.906 (6.4); 0.889 (6.3);
0.146 (1.3); 0.008 (10.0); 0.000 (280.2); -0.008 (11.2); -0.150
(1.3) I-9 3.64 3.66 Example 9: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.544 (9.2); 8.314 (2.7); 8.311 (2.8);
8.294 (2.9); 8.291 (2.8); 7.739 (1.1); 7.735 (1.2); 7.719 (2.5);
7.715 (2.1); 7.701 (2.2); 7.697 (2.1); 7.646 (3.6); 7.627 (2.2);
7.464 (1.9); 7.462 (1.8); 7.444 (3.0); 7.426 (1.6); 7.424 (1.5);
3.322 (31.6); 3.155 (1.9); 3.136 (6.3); 3.118 (6.4); 3.100 (2.0);
2.676 (0.6); 2.671 (0.8); 2.666 (0.6); 2.541 (0.6); 2.524 (2.7);
2.511 (49.3); 2.507 (97.6); 2.502 (126.8); 2.497 (89.7); 2.493
(42.1); 2.333 (0.6); 2.329 (0.8); 2.324 (0.6); 2.075 (0.3); 1.360
(7.3); 1.341 (16.0); 1.323 (7.0); 0.146 (0.3); 0.008 (3.4); 0.000
(84.9); -0.009 (2.9); -0.150 (0.3) I-10 2.08 2.15 Example 10:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.271 (3.7); 8.267
(3.9); 8.137 (2.9); 8.132 (3.0); 7.975 (2.1); 7.954 (3.6); 7.900
(2.2); 7.895 (2.1); 7.880 (1.3); 7.874 (1.3); 6.870 (0.3); 3.977
(15.9); 3.748 (0.9); 3.444 (0.8); 3.327 (95.2); 2.967 (16.0); 2.676
(0.3); 2.671 (0.5); 2.667 (0.3); 2.525 (1.4); 2.507 (54.5); 2.502
(70.2); 2.498 (50.6); 2.494 (24.6); 2.333 (0.3); 2.329 (0.4); 2.184
(0.5); 1.355 (3.8); 1.298 (0.9); 1.259 (1.2); 1.234 (0.6); 0.008
(2.1); 0.000 (54.1); -0.009 (2.3) I-11 2.34 2.39 Example 11:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.279 (0.6); 9.262
(3.9); 8.380 (0.5); 8.317 (0.5); 8.260 (4.2); 8.164 (2.8); 8.159
(3.4); 8.152 (0.5); 8.115 (1.7); 8.110 (1.5); 8.095 (2.1); 8.089
(1.9); 7.937 (3.4); 7.917 (3.0); 7.902 (0.8); 7.897 (0.9); 7.885
(0.5); 7.565 (0.4); 7.545 (0.6); 5.757 (1.6); 3.770 (0.5); 3.747
(16.0); 3.621 (0.4); 3.592 (1.6); 3.445 (15.1); 3.436 (2.1); 3.327
(141.8); 2.675 (0.9); 2.671 (1.2); 2.667 (0.9); 2.524 (4.2); 2.506
(141.2); 2.502 (182.5); 2.498 (131.5); 2.333 (0.8); 2.329 (1.1);
2.324 (0.8); 1.298 (0.8); 1.259 (1.1); 1.235 (0.5); 1.166 (0.3);
0.008 (2.3); 0.000 (56.4); -0.008 (2.3) I-12 1.83 1.88 Example 12:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.272 (4.2); 8.266
(4.5); 8.036 (1.3); 8.023 (1.4); 8.015 (1.6); 8.002 (1.5); 7.966
(1.4); 7.959 (1.6); 7.944 (1.5); 7.937 (1.5); 7.706 (0.8); 7.699
(0.8); 7.685 (1.5); 7.678 (1.5); 7.664 (0.8); 7.657 (0.7); 3.973
(16.0); 3.336 (80.5); 2.958 (16.0); 2.678 (0.4); 2.549 (0.3); 2.509
(67.3); 2.337 (0.4) I-13 2.34 2.44 Example 13: .sup.1H-NMR (400.0
MHz, d.sub.6-DMSO): .delta. = 9.285 (3.9); 8.280 (4.2); 8.088
(2.3); 8.066 (4.9); 8.060 (3.8); 8.009 (2.3); 8.004 (2.0); 7.988
(1.4); 7.983 (1.3); 3.973 (16.0); 3.327 (56.5); 3.313 (1.6); 3.294
(1.2); 3.279 (1.2); 3.261 (1.1); 3.242 (0.3); 2.905 (1.1); 2.886
(1.2); 2.871 (1.0); 2.853 (1.0); 2.671 (0.4); 2.507 (41.3); 2.502
(56.0); 2.498 (43.9); 2.329 (0.4); 1.150 (3.8); 1.132 (8.2); 1.113
(3.7); 0.000 (2.5) I-14 2.63 2.67 Example 14: .sup.1H-NMR (400.0
MHz, d.sub.6-DMSO): .delta. = 9.289 (3.7); 8.430 (1.3); 8.412
(5.2); 8.288 (3.9); 8.287 (3.9); 8.180 (1.6); 8.159 (1.4); 3.772
(16.0); 3.493 (14.4); 3.324 (34.4); 2.524 (0.9); 2.511 (17.9);
2.506 (36.4); 2.502 (48.8); 2.497 (36.6); 2.493 (18.8); 0.008
(1.9); 0.000 (52.6); -0.008 (2.6) I-15 1.92 1.95 Example 15:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.295 (3.5); 9.139
(1.7); 9.135 (1.9); 9.127 (1.9); 9.123 (1.8); 8.579 (1.7); 8.575
(1.8); 8.559 (1.9); 8.555 (1.8); 8.300 (3.6); 8.298 (3.7); 8.021
(1.9); 8.009 (1.8); 8.001 (1.7); 7.989 (1.7); 3.867 (16.0); 3.794
(1.0); 3.775 (3.5); 3.757 (3.5); 3.738 (1.0); 3.327 (10.2); 2.526
(0.5); 2.521 (0.7); 2.512 (10.8); 2.508 (22.2); 2.503 (29.5); 2.499
(21.4); 2.494 (10.4); 1.209 (3.6); 1.191 (7.9); 1.172 (3.5); 0.008
(1.8); 0.000 (50.2); -0.009 (1.9) I-16 3.21 3.26 Example 16:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.588 (2.0); 9.585
(2.1); 9.314 (3.5); 8.780 (2.2); 8.776 (2.2); 8.331 (3.7); 8.316
(0.4); 4.409 (0.3); 4.392 (1.0); 4.375 (1.4); 4.357 (1.0); 4.340
(0.3); 3.914 (16.0); 3.322 (36.9); 2.676 (0.6); 2.671 (0.8); 2.667
(0.6); 2.524 (2.0); 2.520 (3.2); 2.511 (42.6); 2.507 (88.2); 2.502
(118.2); 2.497 (86.9); 2.493 (42.9); 2.333 (0.5); 2.329 (0.7);
2.324 (0.6); 1.260 (13.3); 1.243 (13.2); 0.146 (0.8); 0.008 (6.7);
0.000 (191.2); -0.009 (7.6); -0.150 (0.8) I-17 2.87 2.94 Example
17: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.204 (3.8);
8.228 (4.1); 7.627 (3.7); 7.618 (4.2); 7.536 (1.5); 7.517 (2.1);
7.433 (0.9); 7.422 (1.2); 7.413 (1.2); 7.403 (1.1); 7.392 (0.6);
3.768 (16.0); 3.327 (67.1); 2.986 (1.3); 2.968 (4.1); 2.950 (4.1);
2.931 (1.4); 2.671 (0.5); 2.667 (0.3); 2.507 (57.2); 2.503 (74.4);
2.498 (54.2); 2.334 (0.3); 2.329 (0.5); 2.325 (0.4); 1.180 (4.3);
1.161 (8.7); 1.143 (4.1); 0.146 (0.5); 0.008 (3.9); 0.000 (88.8);
-0.007 (3.9); -0.150 (0.5) I-18 2.11 2.13 Example 18: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.255 (3.5); 8.253 (3.7);
8.251 (3.6); 8.156 (1.3); 8.153 (1.3); 8.138 (1.8); 8.134 (1.6);
8.020 (0.4); 8.017 (0.5); 8.002 (1.4); 7.998 (1.4); 7.984 (1.6);
7.979 (1.5); 7.976 (1.4); 7.971 (1.6); 7.957 (1.5); 7.953 (1.5);
7.938 (0.6); 7.934 (0.5); 7.878 (1.7); 7.875 (1.8); 7.860 (1.2);
7.857 (1.2); 3.728 (16.0); 3.526 (0.5); 3.509 (1.3); 3.490 (1.3);
3.473 (0.5); 3.330 (61.8); 2.671 (0.4); 2.525 (1.2); 2.511 (25.5);
2.507 (50.6); 2.502 (65.3); 2.498 (46.3); 2.493 (21.9); 2.329
(0.4); 1.119 (3.5); 1.101 (7.8); 1.082 (3.4); 0.008 (0.6); 0.000
(15.4); -0.009 (0.6) I-19 3.38 3.43 Example 19: .sup.1H-NMR (400.0
MHz, d.sub.6-DMSO): .delta. = 9.226 (3.9); 8.243 (4.1); 7.705
(0.9); 7.699 (1.3); 7.684 (1.6); 7.678 (2.9); 7.667 (3.6); 7.662
(2.3); 7.640 (3.4); 7.619 (1.8); 3.788 (16.0); 3.323 (25.4); 2.999
(1.2); 2.981 (4.0); 2.963 (4.1); 2.944 (1.3); 2.671 (0.4); 2.626
(0.3); 2.507 (47.1); 2.502 (61.4); 2.498 (45.8); 2.329 (0.4); 2.300
(0.5); 1.177 (4.3); 1.159 (8.9); 1.140 (4.1); 0.008 (1.9); 0.000
(45.5) I-20 2.05 2.08 Example 20: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.258 (4.1); 8.253 (4.3); 7.997 (1.5);
7.990 (2.5); 7.976 (2.4); 7.969 (3.3); 7.956 (1.7); 7.918 (1.1);
7.911 (0.9); 7.897 (1.6); 7.890 (1.4); 7.876 (0.7); 7.869 (0.6);
3.739 (16.0); 3.430 (15.0); 3.326 (81.6); 2.671 (0.7); 2.666 (0.6);
2.506 (84.7); 2.502 (108.3); 2.498 (84.4); 2.328 (0.7); 2.325
(0.5); 0.146 (0.6); 0.000 (128.1); -0.150 (0.6) I-21 2.93 2.98
Example 21: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.586
(2.4); 9.583 (2.5); 9.317 (4.1); 8.798 (2.5); 8.794 (2.6); 8.341
(4.3); 3.925 (16.0); 3.912 (1.3); 3.893 (3.6); 3.874 (3.7); 3.856
(1.1); 3.324 (30.3); 2.671 (0.5); 2.506 (56.1); 2.502 (72.8); 2.498
(55.3); 2.329 (0.5); 1.258 (3.8); 1.239 (8.2); 1.221 (3.7); 0.146
(0.4); 0.007 (3.2); 0.000 (79.6); -0.150 (0.4) I-22 1.87 1.90
Example 22: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.261
(3.9); 8.261 (4.1); 8.107 (1.6); 8.087 (2.0); 7.942 (0.8); 7.940
(1.0); 7.921 (1.7); 7.904 (2.1); 7.901 (2.4); 7.885 (2.2); 7.820
(1.2); 7.818 (1.3); 7.801 (1.6); 7.799 (1.6); 7.783 (0.6); 7.780
(0.7); 5.757 (1.1); 3.946 (16.0); 3.728 (0.5); 3.328 (59.2); 3.305
(1.0); 3.286 (1.1); 3.272 (1.1); 3.253 (1.1); 2.885
(1.1); 2.867 (1.2); 2.852 (1.0); 2.833 (1.0); 2.672 (0.3); 2.507
(37.2); 2.502 (48.9); 2.498 (35.7); 1.149 (3.9); 1.130 (8.2); 1.112
(3.7); 1.102 (0.4); 0.007 (1.5); 0.000 (35.2); -0.008 (1.5) I-23
3.96 4.02 Example 23: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.288 (4.1); 8.977 (2.7); 8.456 (2.7); 8.327 (4.3); 8.317
(0.4); 4.033 (16.0); 3.395 (2.0); 3.377 (2.7); 3.357 (2.4); 3.327
(77.5); 2.720 (2.3); 2.701 (2.8); 2.682 (2.2); 2.672 (0.7); 2.579
(1.5); 2.560 (4.6); 2.542 (4.9); 2.523 (3.2); 2.507 (65.1); 2.502
(87.7); 2.498 (70.2); 2.329 (0.6); 2.075 (0.9); 1.233 (0.6); 1.152
(4.7); 1.133 (9.3); 1.115 (4.4); 0.000 (3.7) I-24 2.32 2.39 Example
24: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.241 (3.7);
8.588 (1.6); 8.585 (1.8); 8.577 (1.7); 8.574 (1.8); 8.279 (3.8);
8.090 (1.5); 8.087 (1.6); 8.069 (1.7); 8.066 (1.8); 7.638 (1.6);
7.627 (1.6); 7.618 (1.5); 7.606 (1.5); 3.975 (16.0); 3.324 (34.0);
3.041 (1.1); 3.022 (3.7); 3.004 (3.8); 2.986 (1.2); 2.672 (0.3);
2.525 (0.8); 2.507 (40.5); 2.503 (55.3); 2.498 (43.4); 2.329 (0.4);
1.218 (4.0); 1.199 (8.3); 1.181 (3.9); 0.008 (1.5); 0.000 (45.1)
I-25 2.97 3.08 Example 25: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.217 (3.6); 8.235 (3.9); 7.564 (2.9); 7.560 (3.0); 7.555
(3.0); 7.544 (3.5); 7.460 (2.0); 7.455 (1.8); 7.440 (1.4); 7.435
(1.3); 3.791 (16.0); 3.323 (28.6); 2.671 (0.3); 2.506 (48.4); 2.502
(56.6); 2.498 (37.8); 2.329 (0.4); 1.398 (0.8); 0.008 (2.5); 0.000
(64.5); -0.008 (2.5) I-26 2.76 2.81 Example 26: .sup.1H-NMR (400.0
MHz, d.sub.6-DMSO): .delta. = 9.389 (2.0); 9.386 (2.0); 9.366
(3.5); 8.849 (2.2); 8.845 (2.1); 8.370 (3.7); 6.870 (0.5); 5.756
(0.4); 4.452 (0.5); 4.347 (15.7); 4.018 (0.6); 3.995 (0.4); 3.326
(80.4); 3.151 (16.0); 2.676 (0.4); 2.671 (0.5); 2.667 (0.3); 2.524
(1.2); 2.511 (28.7); 2.507 (56.3); 2.502 (72.6); 2.498 (52.3);
2.494 (25.3); 2.334 (0.4); 2.329 (0.5); 2.325 (0.3); 2.183 (0.8);
1.355 (5.8); 1.233 (0.6); 0.008 (1.2); 0.000 (33.6); -0.009 (1.3)
I-27 1.84 1.87 Example 27: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.253 (3.5); 8.275 (3.8); 8.273 (3.7); 8.257 (1.5); 8.254
(1.4); 8.237 (1.8); 8.234 (1.7); 8.038 (0.5); 8.035 (0.6); 8.020
(1.5); 8.016 (1.6); 8.001 (1.5); 7.998 (1.3); 7.984 (1.2); 7.980
(1.4); 7.965 (1.6); 7.961 (1.7); 7.946 (0.7); 7.942 (0.6); 7.903
(0.9); 7.895 (2.1); 7.892 (2.0); 7.877 (1.4); 7.873 (1.3); 7.567
(0.4); 7.547 (0.6); 5.756 (8.2); 5.231 (0.7); 5.226 (0.6); 5.216
(0.5); 5.211 (1.3); 5.205 (0.5); 5.196 (0.7); 5.190 (0.8); 5.175
(0.4); 4.802 (2.1); 4.783 (4.1); 4.763 (2.6); 4.673 (2.9); 4.657
(3.1); 4.639 (2.0); 3.746 (16.0); 3.732 (0.5); 3.602 (0.5); 3.594
(0.5); 3.325 (51.0); 2.676 (0.3); 2.671 (0.4); 2.524 (1.2); 2.511
(26.7); 2.507 (53.3); 2.502 (69.4); 2.498 (49.5); 2.493 (23.4);
2.333 (0.3); 2.329 (0.5); 1.760 (0.5); 1.236 (0.7); 1.190 (0.3);
0.000 (2.3) I-28 3.22 3.29 Example 28: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.561 (4.9); 8.983 (2.2); 8.362 (2.2);
8.359 (2.2); 4.075 (16.0); 4.032 (0.3); 4.022 (0.4); 3.323 (56.4);
3.202 (1.1); 3.184 (3.5); 3.165 (3.5); 3.147 (1.1); 2.676 (0.4);
2.671 (0.6); 2.667 (0.4); 2.511 (33.1); 2.507 (65.1); 2.502 (84.7);
2.498 (61.6); 2.494 (30.1); 2.333 (0.4); 2.329 (0.5); 2.324 (0.4);
1.355 (0.7); 1.252 (4.0); 1.233 (8.3); 1.215 (3.7); 0.008 (2.6);
0.000 (63.4); -0.008 (2.5) I-29 2.93 3.04 Example 29: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.302 (3.5); 8.962 (1.6);
8.959 (1.8); 8.951 (1.8); 8.947 (1.8); 8.457 (1.3); 8.437 (1.4);
8.334 (3.7); 7.856 (1.7); 7.845 (1.7); 7.836 (1.6); 7.824 (1.6);
4.092 (16.0); 3.329 (37.7); 2.526 (0.6); 2.512 (14.7); 2.508
(30.1); 2.504 (40.6); 2.499 (31.1); 2.495 (16.5); 0.000 (1.9) I-30
2.36 2.41 Example 30: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.307 (3.8); 8.443 (2.9); 8.305 (4.0); 8.190 (6.5); 4.008
(15.9); 3.327 (62.6); 2.995 (16.0); 2.676 (0.4); 2.671 (0.5); 2.667
(0.4); 2.511 (28.7); 2.507 (57.0); 2.502 (75.3); 2.498 (56.9);
2.334 (0.4); 2.329 (0.5); 2.325 (0.4); 0.000 (3.6) I-31 3.86 3.94
Example 31: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.283
(3.4); 8.955 (2.1); 8.952 (2.1); 8.347 (2.1); 8.343 (2.2); 8.334
(3.8); 4.021 (16.0); 3.324 (17.5); 3.137 (2.1); 3.119 (3.6); 3.101
(2.2); 2.892 (1.6); 2.732 (1.3); 2.672 (0.4); 2.525 (0.7); 2.512
(20.3); 2.507 (42.4); 2.503 (57.6); 2.498 (43.7); 2.494 (22.9);
2.329 (0.4); 1.607 (1.2); 1.588 (2.4); 1.570 (2.5); 1.552 (1.4);
0.961 (4.2); 0.943 (8.6); 0.924 (3.8); 0.008 (1.3); 0.000 (42.0);
-0.009 (2.2) I-32 3.32 3.37 Example 32: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.580 (2.3); 9.577 (2.3); 9.316 (3.9);
8.796 (2.4); 8.792 (2.4); 8.350 (4.1); 7.903 (0.5); 7.898 (0.5);
7.547 (0.5); 5.756 (2.2); 3.923 (16.0); 3.898 (2.3); 3.883 (1.8);
3.878 (2.4); 3.873 (1.8); 3.859 (2.3); 3.775 (0.8); 3.323 (27.3);
2.676 (0.3); 2.671 (0.5); 2.667 (0.3); 2.524 (1.0); 2.511 (25.7);
2.507 (52.2); 2.502 (69.6); 2.498 (51.6); 2.493 (26.0); 2.329
(0.4); 2.324 (0.3); 1.737 (1.1); 1.718 (1.9); 1.699 (2.0); 1.680
(1.2); 1.013 (4.1); 1.002 (0.9); 0.995 (8.4); 0.976 (3.8); 0.000
(9.4); -0.008 (0.4) I-33 2.11 2.12 Example 33: .sup.1H-NMR (400.0
MHz, d.sub.6-DMSO): .delta. = 9.315 (3.7); 8.969 (1.6); 8.966
(1.8); 8.958 (1.8); 8.954 (1.7); 8.556 (1.6); 8.552 (1.7); 8.536
(1.8); 8.532 (1.7); 8.319 (4.0); 7.938 (1.7); 7.926 (1.6); 7.918
(1.6); 7.906 (1.5); 4.318 (16.0); 3.552 (0.9); 3.533 (1.0); 3.519
(1.1); 3.500 (1.1); 3.481 (0.3); 3.324 (25.2); 3.031 (1.1); 3.012
(1.2); 2.998 (1.0); 2.979 (1.0); 2.507 (37.9); 2.503 (49.7); 2.499
(37.5); 1.303 (3.8); 1.285 (8.0); 1.266 (3.7); 0.000 (5.3) I-34
4.41 4.38 Example 34: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.332 (3.7); 8.517 (4.3); 8.515 (4.4); 8.272 (3.7); 8.251
(3.9); 7.627 (0.5); 7.623 (0.6); 7.614 (0.4); 7.597 (0.5); 7.575
(0.4); 7.566 (0.4); 7.556 (0.4); 7.542 (2.9); 7.538 (3.4); 7.509
(2.4); 7.504 (1.7); 7.488 (2.1); 7.483 (1.8); 3.321 (35.3); 2.680
(0.4); 2.675 (0.9); 2.671 (1.2); 2.666 (0.8); 2.662 (0.4); 2.610
(16.0); 2.524 (3.5); 2.511 (65.6); 2.506 (129.9); 2.502 (168.9);
2.497 (120.0); 2.493 (56.5); 2.337 (0.4); 2.333 (0.8); 2.329 (1.1);
2.324 (0.8); 2.320 (0.4); 1.355 (1.2); 1.328 (0.4); 1.207 (0.3);
1.189 (0.7); 1.168 (2.5); 1.160 (2.3); 1.145 (0.4); 1.058 (0.5);
0.146 (0.4); 0.008 (3.6); 0.000 (97.2); -0.009 (3.2); -0.150 (0.4)
I-35 4.07 4.03 Example 35: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.334 (5.6); 8.540 (6.8); 8.538 (6.7); 8.234 (2.7); 8.231
(2.8); 8.214 (3.0); 8.211 (2.8); 7.693 (1.0); 7.690 (1.0); 7.673
(2.6); 7.669 (2.1); 7.655 (2.3); 7.651 (2.2); 7.621 (3.9); 7.602
(2.0); 7.440 (1.8); 7.437 (1.8); 7.420 (3.0); 7.402 (1.5); 7.399
(1.4); 3.323 (126.5); 3.130 (2.0); 3.112 (6.6); 3.093 (6.7); 3.075
(2.1); 2.680 (0.5); 2.675 (1.1); 2.671 (1.5); 2.666 (1.1); 2.662
(0.5); 2.524 (4.8); 2.511 (84.8); 2.506 (166.1); 2.502 (215.2);
2.497 (153.7); 2.493 (72.9); 2.333 (1.0); 2.329 (1.4); 2.324 (1.0);
1.333 (7.5); 1.315 (16.0); 1.297 (7.2); 0.008 (1.0); 0.000 (28.0);
-0.009 (0.9) I-36 2.64 2.67 Example 36: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.577 (2.7); 9.575 (2.7); 9.320 (4.2);
8.825 (2.8); 8.822 (2.8); 8.347 (4.5); 7.902 (0.7); 7.897 (0.7);
7.886 (0.4); 7.566 (0.3); 7.546 (0.5); 5.757 (1.3); 4.018 (1.1);
3.934 (16.0); 3.700 (15.4); 3.325 (73.6); 2.671 (0.7); 2.506
(74.4); 2.502 (95.9); 2.498 (76.5); 2.328 (0.6); 1.258 (0.3); 1.236
(1.0); 1.169 (0.8); 0.000 (2.4) I-37 3.10 3.17 Example 37:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.392 (2.2); 9.388
(2.3); 9.369 (3.8); 8.726 (2.3); 8.721 (2.4); 8.385 (3.9); 8.316
(0.5); 4.362 (16.0); 3.627 (0.9); 3.608 (1.1); 3.594 (1.1); 3.575
(1.0); 3.324 (136.2); 3.117 (1.0); 3.098 (1.2); 3.084 (1.0); 3.065
(0.9); 2.676 (0.8); 2.671 (1.1); 2.667 (0.9); 2.507 (127.4); 2.502
(169.6); 2.498 (129.7); 2.333 (0.8); 2.329 (1.1); 2.325 (0.9);
1.330 (3.8); 1.312 (8.1); 1.293 (3.6); 0.146 (0.9); 0.008 (7.7);
0.000 (196.4); -0.150 (0.9) I-38 2.63 2.68 Example 38: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.273 (3.9); 8.266 (4.2);
8.141 (2.4); 8.120 (3.8); 8.105 (2.9); 8.100 (3.4); 8.055 (2.4);
8.049 (2.0); 8.033 (1.5); 8.028 (1.3); 7.904 (0.8); 7.899 (0.7);
7.894 (0.5); 7.887 (0.5); 7.697 (0.3); 7.568 (0.5); 7.548 (0.8);
7.528 (0.3); 3.763 (16.0); 3.530 (0.6); 3.513 (1.3); 3.495 (1.4);
3.476 (0.6); 3.357 (0.5); 3.328 (61.7); 2.676 (0.4); 2.671 (0.5);
2.667 (0.4); 2.525 (1.3); 2.507 (57.0); 2.502 (75.7); 2.498 (56.3);
2.333 (0.3); 2.329 (0.5); 2.325 (0.3); 1.125 (3.8); 1.107 (8.1);
1.088 (3.6); 0.000 (0.6) I-39 3.45 3.52 Example 39: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.386 (2.2); 9.383 (2.3);
9.374 (3.8); 8.774 (2.3); 8.769 (2.3); 8.316 (0.4); 8.302 (3.8);
5.756 (0.4); 4.362 (16.0); 3.637 (0.5); 3.616 (0.9); 3.605 (0.6);
3.596 (0.6); 3.585 (1.0); 3.564 (0.6); 3.322 (68.3); 2.993 (0.6);
2.981 (0.7); 2.973 (0.7); 2.961 (1.1); 2.949 (0.7); 2.941 (0.7);
2.928 (0.6); 2.676 (0.6); 2.671 (0.8); 2.666 (0.6); 2.511 (49.6);
2.506 (97.4); 2.502 (127.7); 2.497 (95.5); 2.493 (49.9); 2.333
(0.6); 2.329 (0.8); 2.324 (0.6); 2.029 (0.5); 2.010 (0.7); 1.994
(0.8); 1.975 (0.7); 1.956 (0.4); 1.804 (0.4); 1.789 (0.6); 1.783
(0.5); 1.770 (0.6); 1.757 (0.4); 1.754 (0.4); 1.146 (3.8); 1.128
(8.0); 1.109 (3.6); 0.146 (0.8); 0.008 (8.1); 0.000 (174.8); -0.008
(10.0); -0.150 (0.8) I-40 3.10 3.15 Example 40: .sup.1H-NMR (400.0
MHz, d.sub.6-DMSO): .delta. = 9.347 (4.8); 8.561 (5.7); 8.293
(2.2); 8.291 (2.3); 8.274 (2.4); 8.271 (2.3); 7.668 (1.0); 7.665
(1.1); 7.647 (2.2); 7.630 (1.4); 7.627 (1.3); 7.480 (1.7); 7.460
(2.8); 7.442 (1.3); 7.179 (2.9); 7.159 (2.6); 6.870 (1.5); 6.647
(0.8); 5.165 (3.3); 5.147 (6.3); 5.130 (3.6); 4.804 (0.5); 4.788
(1.2); 4.771 (1.9); 4.755 (1.2); 4.738 (0.4); 4.512 (3.8); 4.496
(6.3); 4.480 (3.3); 3.328 (53.8); 2.672 (0.6); 2.507 (73.4); 2.503
(93.5); 2.499 (70.8); 2.330 (0.6); 2.183 (2.4); 1.355 (16.0); 1.233
(0.9); 1.182 (0.6); 0.008 (3.2); 0.000 (57.9) I-41 3.73 3.80
Example 41: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.277
(3.9); 8.989 (2.5); 8.456 (2.5); 8.453 (2.5); 8.345 (0.3); 8.333
(4.2); 7.954 (0.5); 4.021 (0.4); 4.003 (1.1); 3.988 (16.0); 3.949
(0.4); 3.932 (1.0); 3.916 (1.4); 3.899 (1.1); 3.883 (0.4); 3.325
(35.1); 2.892 (3.7); 2.732 (3.3); 2.672 (0.3); 2.507 (40.5); 2.503
(53.7); 2.499 (41.6); 2.330 (0.4); 1.235 (14.8); 1.219 (14.7);
0.008 (1.4); 0.000 (30.8) I-42 3.39 3.46 Example I-42: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.881 (0.4); 9.213 (3.4);
8.238 (3.6); 8.236 (3.6); 8.136 (0.4); 8.085 (0.7); 7.683 (0.3);
7.639 (2.8); 7.634 (2.9); 7.572 (2.4); 7.552 (3.7); 7.504 (0.5);
7.499 (0.5); 7.483 (2.1); 7.478 (2.0); 7.462 (1.4); 7.457 (1.3);
6.870 (0.4); 3.779 (16.0); 3.618 (0.4); 3.608 (0.3); 3.602 (1.0);
3.585 (0.4); 3.325 (20.2); 3.098 (0.6); 3.067 (1.2); 3.048 (3.9);
3.030 (4.0); 3.016 (0.9); 3.012 (1.3); 2.877 (1.1); 2.865 (1.1);
2.676 (0.4); 2.671 (0.5); 2.667 (0.4); 2.525 (1.4); 2.520 (2.1);
2.511 (30.1); 2.507
(61.5); 2.502 (81.2); 2.498 (58.8); 2.493 (28.4); 2.333 (0.4);
2.329 (0.5); 2.324 (0.4); 2.183 (0.7); 1.776 (0.4); 1.769 (0.4);
1.760 (1.2); 1.752 (0.4); 1.744 (0.4); 1.355 (5.3); 1.245 (0.8);
1.236 (0.4); 1.226 (1.7); 1.218 (0.5); 1.208 (0.8); 1.193 (4.1);
1.175 (8.7); 1.156 (3.9); 0.146 (0.4); 0.008 (2.9); 0.000 (88.8);
-0.009 (3.1); -0.150 (0.4) I-43 2.61 2.69 Example I-43: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.259 (3.8); 8.259 (4.0);
8.123 (6.1); 8.118 (3.1); 8.107 (2.5); 8.102 (1.5); 7.945 (2.9);
7.939 (0.8); 7.929 (0.7); 7.923 (2.3); 5.757 (11.4); 3.742 (16.0);
3.600 (0.7); 3.581 (2.2); 3.563 (2.2); 3.545 (0.7); 3.329 (38.9);
2.671 (0.4); 2.525 (1.2); 2.511 (23.7); 2.507 (48.0); 2.502 (63.6);
2.498 (47.5); 2.494 (24.1); 2.329 (0.4); 1.146 (3.7); 1.128 (8.2);
1.109 (3.6); 0.008 (0.3); 0.000 (9.3); -0.008 (0.4) I-44 2.36 2.45
Example I-44: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. =
9.270 (3.8); 8.317 (0.5); 8.273 (4.1); 8.022 (2.9); 8.016 (3.1);
7.986 (2.2); 7.966 (3.6); 7.905 (2.1); 7.899 (1.9); 7.884 (1.3);
7.879 (1.2); 3.969 (16.0); 3.377 (1.0); 3.359 (1.3); 3.344 (1.9);
3.329 (150.3); 3.307 (0.6); 2.945 (1.1); 2.927 (1.2); 2.912 (1.0);
2.893 (0.9); 2.676 (0.9); 2.671 (1.2); 2.667 (0.9); 2.524 (3.1);
2.507 (141.2); 2.502 (185.0); 2.498 (135.5); 2.333 (0.9); 2.329
(1.2); 2.325 (0.9); 1.179 (3.8); 1.160 (8.2); 1.142 (3.7); 0.008
(2.3); 0.000 (70.9); -0.009 (2.6); -0.150 (0.3) I-45 2.53 Example
I-45: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.295 (3.9);
8.364 (3.2); 8.342 (3.4); 8.292 (4.1); 7.347 (3.4); 7.325 (3.3);
4.015 (1.0); 3.987 (16.0); 3.922 (15.6); 3.910 (1.3); 3.733 (1.0);
3.714 (3.4); 3.695 (3.4); 3.677 (1.0); 3.506 (0.3); 3.331 (66.6);
2.672 (0.5); 2.668 (0.4); 2.507 (58.9); 2.503 (75.4); 2.498 (56.9);
2.334 (0.4); 2.329 (0.5); 2.325 (0.4); 2.087 (2.0); 1.234 (0.8);
1.203 (3.6); 1.185 (7.9); 1.166 (3.5); 0.008 (2.1); 0.000 (43.3)
I-46 2.92 2.98 Example I-46: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.269 (4.1); 8.592 (1.8); 8.590 (1.9); 8.581 (1.9); 8.578
(1.8); 8.306 (4.3); 8.094 (1.7); 8.092 (1.7); 8.074 (1.9); 8.071
(1.8); 7.955 (0.8); 7.642 (1.6); 7.631 (1.6); 7.622 (1.5); 7.610
(1.5); 3.979 (16.0); 3.334 (9.6); 3.046 (1.2); 3.027 (3.8); 3.009
(3.9); 2.991 (1.3); 2.893 (4.9); 2.734 (4.4); 2.509 (22.7); 2.505
(28.6); 2.501 (21.4); 1.220 (4.2); 1.202 (8.6); 1.184 (4.1); 0.000
(4.6) I-47 4.02 4.10 Example I-47: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.308 (3.5); 8.964 (2.1); 8.961 (2.1);
8.355 (3.9); 8.353 (3.9); 8.341 (2.2); 8.338 (2.2); 8.317 (0.3);
4.030 (16.0); 3.328 (183.2); 3.184 (1.1); 3.165 (3.5); 3.147 (3.6);
3.129 (1.1); 2.676 (0.8); 2.671 (1.1); 2.667 (0.8); 2.525 (2.5);
2.520 (3.8); 2.511 (53.3); 2.507 (109.8); 2.502 (147.2); 2.498
(110.1); 2.494 (55.4); 2.334 (0.7); 2.329 (1.0); 2.325 (0.7); 1.235
(4.2); 1.217 (8.3); 1.198 (3.8); 0.146 (1.1); 0.008 (8.0); 0.000
(229.8); -0.009 (9.5); -0.150 (1.1) I-48 2.64 2.70 Example I-48:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.337 (2.2); 9.324
(2.3); 9.295 (4.0); 8.366 (2.9); 8.353 (2.8); 8.273 (4.3); 5.757
(0.8); 3.919 (16.0); 3.894 (0.7); 3.879 (1.3); 3.862 (1.3); 3.327
(92.4); 2.676 (0.6); 2.671 (0.8); 2.667 (0.6); 2.507 (88.5); 2.502
(113.9); 2.498 (86.6); 2.333 (0.6); 2.329 (0.8); 2.325 (0.6); 1.243
(3.6); 1.224 (7.4); 1.206 (3.4); 0.146 (0.6); 0.008 (6.3); 0.000
(128.4); -0.150 (0.6) I-49 1.99 2.05 Example I-49: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 11.328 (3.1); 9.295 (4.3);
8.532 (1.7); 8.509 (4.8); 8.487 (4.4); 8.465 (1.5); 8.318 (0.6);
8.304 (4.7); 3.876 (16.0); 3.847 (0.7); 3.658 (1.1); 3.639 (3.5);
3.621 (3.5); 3.602 (1.1); 3.331 (78.4); 2.892 (0.3); 2.676 (1.0);
2.672 (1.3); 2.668 (1.0); 2.565 (0.4); 2.507 (157.3); 2.503
(200.0); 2.498 (150.8); 2.344 (0.8); 2.334 (1.0); 2.329 (1.4);
2.169 (15.8); 1.989 (1.1); 1.234 (0.5); 1.184 (3.8); 1.175 (1.3);
1.166 (8.3); 1.148 (3.7); 0.008 (0.9); 0.000 (19.7) I-50 2.27 2.39
Example I-50: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. =
10.770 (2.6); 9.256 (3.9); 8.290 (1.9); 8.277 (4.3); 8.268 (2.5);
8.242 (0.7); 8.115 (3.0); 8.093 (2.4); 8.063 (0.4); 4.456 (1.9);
4.038 (0.6); 4.020 (0.7); 3.979 (16.0); 3.332 (83.1); 2.966 (1.2);
2.948 (4.0); 2.929 (4.1); 2.911 (1.3); 2.676 (0.4); 2.672 (0.5);
2.668 (0.4); 2.507 (62.3); 2.503 (81.2); 2.498 (61.4); 2.334 (0.4);
2.330 (0.5); 2.325 (0.4); 2.184 (1.9); 2.119 (15.2); 1.989 (2.6);
1.193 (0.7); 1.172 (4.5); 1.154 (9.1); 1.135 (4.2); 0.008 (2.6);
0.000 (55.6); -0.008 (3.1) I-51 2.48 Example I-51: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.259 (4.5); 9.210 (2.4);
9.198 (2.5); 8.278 (4.7); 8.276 (4.8); 8.226 (3.2); 8.214 (3.1);
5.757 (2.5); 3.965 (0.7); 3.946 (0.8); 3.932 (0.8); 3.920 (0.7);
3.914 (0.8); 3.795 (16.0); 3.375 (0.6); 3.356 (0.8); 3.328 (59.8);
3.305 (0.3); 2.676 (0.4); 2.672 (0.5); 2.667 (0.4); 2.525 (1.2);
2.511 (27.2); 2.507 (56.1); 2.502 (75.0); 2.498 (55.5); 2.494
(27.5); 2.334 (0.4); 2.329 (0.5); 2.325 (0.4); 1.264 (3.7); 1.245
(7.9); 1.227 (3.8); 0.008 (1.2); 0.000 (39.0); -0.008 (1.4) I-52
2.51 2.61 Example I-52: .sup.1H-NMR (601.6 MHz, CD3CN): .delta. =
9.321 (2.5); 8.780 (3.9); 8.736 (2.6); 7.746 (3.8); 3.824 (1.3);
3.809 (16.0); 3.799 (3.9); 3.787 (1.3); 2.141 (2.3); 1.965 (10.4);
1.957 (0.4); 1.944 (3.9); 1.940 (5.2); 1.937 (3.8); 1.933 (2.0);
1.297 (3.8); 1.285 (7.6); 1.273 (3.7); 0.000 (3.3) I-53 3.12
Example I-53: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. =
9.242 (3.5); 8.270 (3.7); 8.119 (0.4); 8.064 (2.9); 8.042 (3.1);
7.123 (3.3); 7.101 (3.1); 4.012 (16.0); 3.959 (0.4); 3.909 (1.6);
3.899 (16.0); 3.332 (95.1); 2.942 (1.2); 2.923 (3.9); 2.905 (3.9);
2.887 (1.3); 2.677 (0.4); 2.672 (0.6); 2.668 (0.4); 2.525 (1.6);
2.511 (32.5); 2.507 (64.4); 2.503 (84.3); 2.499 (63.2); 2.334
(0.4); 2.330 (0.6); 2.325 (0.4); 1.990 (0.8); 1.175 (0.5); 1.144
(4.1); 1.126 (8.6); 1.107 (4.0); 0.008 (2.3); 0.000 (60.3); -0.008
(3.0) I-54 3.07 3.16 Example I-54: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.293 (3.9); 8.987 (2.7); 8.490 (2.7);
8.335 (4.1); 5.757 (0.6); 4.713 (1.2); 4.699 (2.4); 4.685 (1.2);
4.595 (1.1); 4.581 (2.3); 4.567 (1.3); 4.041 (16.0); 3.581 (1.1);
3.567 (2.2); 3.553 (1.1); 3.521 (1.2); 3.507 (2.2); 3.493 (1.1);
3.327 (105.4); 2.671 (0.8); 2.506 (88.1); 2.502 (120.1); 2.498
(96.8); 2.333 (0.6); 2.329 (0.8); 1.234 (0.4); 0.146 (0.4); 0.008
(2.7); 0.000 (84.4); -0.150 (0.4) I-55 3.01 3.12 Example I-55:
.sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 8.956 (3.9); 8.953
(4.0); 8.942 (2.0); 8.940 (2.0); 8.317 (2.1); 7.904 (3.7); 7.902
(3.7); 3.950 (16.0); 3.332 (109.0); 3.172 (1.0); 3.154 (3.3); 3.135
(3.4); 3.117 (1.0); 2.676 (0.3); 2.672 (0.5); 2.667 (0.4); 2.525
(1.2); 2.520 (1.8); 2.512 (26.2); 2.507 (53.9); 2.503 (71.3); 2.498
(52.0); 2.494 (25.3); 2.334 (0.3); 2.330 (0.5); 2.325 (0.4); 1.251
(0.5); 1.232 (5.1); 1.214 (7.9); 1.195 (3.5); 1.103 (0.3); 0.000
(6.1) I-56 1.56 1.61 Example I-56: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.502 (3.9); 9.497 (3.4); 9.306 (4.1);
8.900 (4.0); 8.895 (3.4); 8.645 (1.9); 8.322 (4.5); 8.057 (1.9);
3.892 (16.0); 3.843 (1.3); 3.825 (3.8); 3.806 (3.7); 3.788 (1.1);
3.332 (180.7); 2.676 (0.9); 2.672 (1.1); 2.667 (0.8); 2.507
(135.9); 2.503 (156.6); 2.498 (111.5); 2.334 (0.9); 2.330 (1.0);
2.325 (0.7); 1.298 (0.5); 1.259 (1.0); 1.235 (5.5); 1.217 (8.5);
1.198 (3.8); 0.000 (14.4); -0.062 (0.6) I-57 2.82 2.89 Example
I-57: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.596 (2.3);
9.593 (2.2); 9.330 (3.8); 9.320 (0.5); 8.830 (2.3); 8.826 (2.2);
8.353 (4.1); 4.994 (1.0); 4.982 (1.5); 4.969 (1.1); 4.877 (1.0);
4.865 (1.5); 4.852 (1.2); 4.493 (1.1); 4.480 (1.5); 4.468 (1.0);
4.427 (1.2); 4.414 (1.5); 4.402 (1.0); 3.957 (16.0); 3.947 (1.6);
3.919 (0.4); 3.813 (0.3); 3.328 (182.7); 2.676 (0.7); 2.671 (1.0);
2.667 (0.7); 2.663 (0.4); 2.524 (3.6); 2.511 (61.5); 2.507 (120.1);
2.502 (156.5); 2.498 (114.9); 2.493 (57.0); 2.333 (0.7); 2.329
(1.0); 2.325 (0.7); 2.074 (0.5); 1.235 (0.6); 0.008 (2.3); 0.000
(63.1); -0.008 (2.5) I-58 2.19 Example I-58: .sup.1H-NMR (400.0
MHz, d.sub.6-DMSO): .delta. = 9.553 (2.2); 9.550 (2.2); 9.320
(3.9); 8.786 (2.4); 8.781 (2.4); 8.336 (4.1); 5.755 (1.0); 5.119
(1.2); 5.106 (2.9); 5.093 (1.3); 4.066 (1.6); 4.052 (3.3); 4.038
(2.1); 3.919 (16.0); 3.869 (1.1); 3.855 (2.7); 3.842 (2.5); 3.828
(0.9); 3.400 (0.4); 3.393 (0.4); 3.384 (0.5); 3.345 (268.1); 3.309
(0.6); 2.672 (0.4); 2.526 (1.1); 2.512 (22.7); 2.508 (46.1); 2.503
(61.2); 2.499 (45.2); 2.494 (22.6); 2.330 (0.4); 0.000 (0.6) I-59
2.31 2.41 Example I-59: .sup.1H-NMR (600.1 MHz, CD3CN): .delta. =
9.085 (2.6); 8.843 (1.4); 8.842 (1.6); 8.840 (1.5); 8.333 (1.7);
8.331 (1.6); 8.165 (2.9); 5.447 (1.4); 3.979 (16.0); 3.725 (0.9);
3.715 (2.8); 3.705 (2.9); 3.695 (1.0); 3.459 (0.9); 3.449 (1.8);
3.439 (0.8); 3.177 (2.4); 3.167 (4.3); 3.157 (2.2); 2.145 (5.7);
1.957 (0.5); 1.953 (0.6); 1.949 (3.0); 1.945 (5.2); 1.941 (7.5);
1.937 (5.0); 1.933 (2.5) I-60 1.76 1.77 Example I-60: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.262 (4.0); 8.968 (3.2);
8.963 (3.3); 8.415 (1.6); 8.354 (3.0); 8.350 (3.1); 8.303 (4.3);
7.862 (1.6); 4.008 (16.0); 3.331 (33.2); 3.113 (1.1); 3.095 (3.7);
3.076 (3.8); 3.058 (1.2); 2.508 (35.4); 2.504 (46.2); 2.499 (34.8);
1.246 (4.0); 1.228 (8.5); 1.209 (3.9); 0.008 (1.7); 0.000 (46.1);
-0.008 (2.2) I-61 2.63 2.71 Example I-61: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.343 (3.7); 8.973 (1.6); 8.969 (1.8);
8.961 (1.8); 8.957 (1.8); 8.559 (1.6); 8.555 (1.7); 8.539 (1.8);
8.535 (1.8); 8.347 (4.0); 8.345 (4.0); 7.941 (1.7); 7.929 (1.6);
7.921 (1.6); 7.909 (1.6); 4.320 (16.0); 3.561 (1.0); 3.542 (1.0);
3.528 (1.1); 3.509 (1.1); 3.490 (0.3); 3.330 (33.2); 3.048 (1.1);
3.030 (1.2); 3.015 (1.0); 2.997 (1.0); 2.677 (0.4); 2.672 (0.5);
2.668 (0.4); 2.525 (1.3); 2.507 (56.6); 2.503 (75.2); 2.499 (56.4);
2.334 (0.4); 2.330 (0.5); 2.325 (0.4); 1.301 (3.8); 1.282 (8.2);
1.264 (3.7); 0.146 (0.5); 0.008 (4.0); 0.000 (110.8); -0.008 (5.6);
-0.150 (0.5) I-62 2.15 2.17 Example I-62: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.207 (3.4); 8.318 (0.5); 8.194 (3.7);
8.192 (3.6); 8.062 (1.6); 8.059 (1.7); 8.042 (2.2); 8.039 (2.2);
7.947 (1.8); 7.928 (2.7); 7.908 (1.6); 7.735 (2.0); 7.732 (2.1);
7.716 (1.8); 7.713 (1.7); 3.742 (16.0); 3.593 (1.0); 3.574 (3.5);
3.556 (3.6); 3.537 (1.2); 3.329 (74.8); 2.676 (0.7); 2.671 (0.9);
2.667 (0.7); 2.662 (0.4); 2.525 (2.4); 2.520 (3.6); 2.511 (50.5);
2.507 (105.6); 2.502 (140.5); 2.498 (101.4); 2.493 (48.8); 2.334
(0.6); 2.329 (0.9); 2.324 (0.6); 2.086 (0.7); 1.235 (1.3); 1.184
(4.0); 1.166 (9.0); 1.147 (3.9); 1.140 (0.6); 0.146 (0.7); 0.008
(5.0); 0.000 (161.5); -0.009 (5.9); -0.150 (0.7) I-63 3.62 3.75
Example I-63: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. =
9.396 (5.6); 8.728 (2.2); 8.723 (2.3); 8.416 (4.1); 8.414 (3.9);
8.318 (0.5); 4.362 (16.0); 3.635 (0.9); 3.617 (1.0); 3.602 (1.1);
3.583 (1.0); 3.332 (165.3); 3.134 (1.0); 3.116 (1.2); 3.101 (1.0);
3.083 (1.0); 2.676 (0.8); 2.672 (1.1); 2.667 (0.8); 2.525 (2.6);
2.511 (62.1); 2.507 (126.3); 2.503 (165.5); 2.498 (121.7); 2.494
(60.8); 2.334 (0.8); 2.329 (1.1); 2.325 (0.8); 1.327 (3.7); 1.308
(8.1); 1.290 (3.6);
0.146 (0.4); 0.008 (3.1); 0.000 (96.0); -0.008 (4.1); -0.150 (0.4)
I-64 3.95 3.93 Example I-64: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.275 (2.6); 9.271 (2.5); 8.943 (4.3); 8.584 (2.6); 8.580
(2.6); 8.318 (0.5); 7.701 (3.0); 7.680 (3.9); 7.548 (3.8); 7.527
(3.0); 7.410 (4.6); 3.890 (16.0); 3.329 (75.4); 3.140 (1.3); 3.122
(4.2); 3.104 (4.3); 3.086 (1.4); 2.676 (0.9); 2.671 (1.2); 2.667
(0.9); 2.507 (140.3); 2.502 (179.9); 2.498 (134.5); 2.334 (0.9);
2.329 (1.2); 2.325 (0.9); 1.281 (4.6); 1.263 (9.7); 1.245 (4.5);
0.146 (0.4); 0.008 (3.6); 0.000 (84.0); -0.150 (0.4) I-65 4.31 4.37
Example I-65: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. =
9.217 (3.1); 9.076 (4.1); 9.074 (4.1); 8.959 (2.3); 8.956 (2.3);
8.334 (2.3); 8.318 (1.7); 8.288 (3.7); 8.211 (4.1); 8.209 (4.1);
5.758 (1.1); 4.005 (16.0); 3.328 (226.4); 3.189 (1.1); 3.171 (3.5);
3.153 (3.6); 3.134 (1.1); 2.676 (2.7); 2.671 (3.8); 2.667 (2.8);
2.525 (9.3); 2.520 (14.6); 2.511 (211.4); 2.507 (434.4); 2.502
(573.8); 2.498 (421.2); 2.493 (209.9); 2.333 (2.7); 2.329 (3.7);
2.324 (2.8); 1.258 (0.3); 1.243 (4.1); 1.225 (8.8); 1.206 (3.9);
1.148 (0.3); 0.146 (1.3); 0.008 (9.7); 0.000 (308.8); -0.008
(13.1); -0.150 (1.4) I-66 3.42 3.50 Example I-66: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.243 (3.5); 8.317 (0.4);
8.274 (3.7); 8.069 (2.9); 8.047 (3.1); 7.116 (3.3); 7.094 (3.2);
4.017 (0.4); 4.000 (16.0); 3.893 (15.8); 3.329 (74.5); 2.884 (2.3);
2.867 (3.7); 2.848 (2.4); 2.676 (0.7); 2.671 (0.9); 2.667 (0.7);
2.525 (2.3); 2.511 (50.8); 2.507 (105.0); 2.502 (139.6); 2.498
(102.9); 2.494 (51.4); 2.334 (0.6); 2.329 (0.9); 2.325 (0.7); 1.496
(1.2); 1.478 (2.4); 1.460 (2.5); 1.442 (1.4); 0.875 (4.2); 0.857
(8.4); 0.838 (3.7); 0.008 (0.8); 0.000 (28.2); -0.008 (1.2) I-67
2.70 2.75 Example I-67: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 10.028 (0.5); 9.850 (0.4); 9.268 (0.7); 9.248 (3.0);
8.317 (1.0); 8.302 (0.7); 8.262 (3.1); 8.236 (0.6); 8.194 (0.5);
8.119 (1.3); 8.097 (0.7); 8.026 (2.6); 8.004 (2.6); 7.996 (0.5);
7.978 (0.6); 7.181 (0.8); 7.159 (0.6); 7.133 (2.8); 7.111 (2.7);
4.442 (2.5); 4.071 (13.8); 4.017 (3.3); 4.014 (3.6); 3.959 (1.9);
3.910 (16.0); 3.329 (346.6); 2.881 (1.4); 2.869 (1.4); 2.676 (1.7);
2.671 (2.3); 2.667 (1.7); 2.525 (5.8); 2.511 (128.4); 2.507
(263.1); 2.502 (348.1); 2.498 (256.2); 2.494 (127.6); 2.422 (14.2);
2.334 (1.7); 2.329 (2.3); 2.325 (1.7); 1.989 (0.9); 1.234 (0.3);
1.175 (0.5); 0.146 (0.4); 0.008 (3.2); 0.000 (99.9); -0.008 (3.8);
-0.150 (0.5) I-68 2.46 2.50 Example I-68: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.319 (4.1); 9.142 (1.6); 9.139 (1.9);
9.130 (1.8); 9.126 (1.9); 8.582 (1.6); 8.578 (1.8); 8.562 (1.9);
8.558 (1.9); 8.328 (4.3); 8.024 (1.7); 8.012 (1.7); 8.003 (1.6);
7.991 (1.6); 3.870 (16.0); 3.802 (1.0); 3.783 (3.5); 3.765 (3.6);
3.746 (1.1); 3.333 (44.0); 2.676 (0.3); 2.672 (0.5); 2.668 (0.4);
2.507 (56.6); 2.503 (74.8); 2.499 (56.9); 2.330 (0.5); 1.209 (3.7);
1.191 (8.1); 1.172 (3.6); 0.008 (1.1); 0.000 (28.7) I-69 4.32 4.37
Example I-69: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. =
9.080 (4.3); 9.078 (4.2); 8.959 (2.4); 8.956 (2.4); 8.873 (1.8);
8.871 (2.0); 8.867 (2.1); 8.865 (1.8); 8.337 (2.4); 8.334 (2.4);
8.181 (4.2); 8.180 (4.2); 7.062 (2.5); 7.056 (2.5); 4.007 (16.0);
3.330 (22.5); 3.189 (1.1); 3.170 (3.7); 3.152 (3.7); 3.133 (1.2);
2.677 (0.3); 2.672 (0.5); 2.668 (0.3); 2.526 (1.2); 2.512 (26.3);
2.508 (53.3); 2.503 (70.1); 2.499 (51.8); 2.495 (26.3); 2.330
(0.4); 2.326 (0.3); 2.077 (0.6); 1.244 (4.0); 1.225 (8.7); 1.207
(3.9); 0.008 (1.3); 0.000 (37.3); -0.008 (1.8) I-70 3.24 3.29
Example I-70: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. =
9.272 (4.0); 9.057 (2.0); 9.044 (2.1); 8.309 (4.2); 8.135 (2.8);
8.122 (2.7); 4.021 (0.4); 3.846 (16.0); 3.328 (22.9); 2.736 (1.1);
2.717 (3.4); 2.699 (3.5); 2.680 (1.3); 2.507 (37.7); 2.503 (49.4);
2.499 (37.9); 1.990 (1.3); 1.397 (1.1); 1.193 (0.3); 1.176 (0.7);
1.158 (0.4); 0.985 (4.0); 0.966 (8.1); 0.948 (3.8); 0.008 (1.7);
0.000 (44.7); -0.008 (2.1) I-71 2.93 Example I-71: .sup.1H-NMR
(400.0 MHz, d.sub.6-DMSO): .delta. = 9.293 (4.1); 8.368 (3.1);
8.345 (3.3); 8.299 (4.3); 7.342 (3.4); 7.320 (3.2); 5.758 (0.9);
4.017 (0.4); 3.985 (16.0); 3.918 (15.5); 3.716 (2.2); 3.701 (1.9);
3.696 (2.5); 3.692 (1.8); 3.677 (2.2); 3.330 (25.0); 2.676 (0.4);
2.672 (0.5); 2.668 (0.4); 2.507 (54.4); 2.503 (69.4); 2.499 (51.7);
2.330 (0.5); 2.326 (0.3); 1.668 (1.1); 1.649 (2.0); 1.630 (2.0);
1.611 (1.2); 1.235 (0.7); 0.993 (4.1); 0.974 (8.2); 0.956 (3.7);
0.000 (2.4) I-72 2.26 2.32 Example I-72: .sup.1H-NMR (400.0 MHz,
d.sub.6-DMSO): .delta. = 9.581 (3.0); 9.576 (3.0); 9.312 (4.1);
9.070 (3.3); 9.065 (3.2); 8.716 (1.0); 8.704 (0.9); 8.335 (4.3);
8.091 (0.4); 7.660 (0.6); 7.645 (0.8); 7.641 (0.7); 7.626 (0.6);
3.916 (16.0); 3.872 (1.3); 3.854 (3.8); 3.835 (3.9); 3.817 (1.4);
3.736 (0.6); 3.694 (0.7); 3.626 (0.8); 3.613 (0.8); 2.671 (1.0);
2.506 (105.6); 2.502 (135.4); 2.498 (103.6); 2.333 (0.7); 2.329
(0.9); 1.989 (0.7); 1.298 (0.6); 1.252 (4.0); 1.234 (9.7); 1.215
(3.9); 1.193 (0.3); 1.175 (0.5); 0.000 (3.0) I-73 2.20 2.25 Example
I-73: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): .delta. = 9.297 (3.6);
9.268 (0.9); 9.255 (0.6); 9.208 (0.4); 8.404 (3.2); 8.382 (3.4);
8.317 (0.4); 8.298 (3.9); 8.238 (0.6); 8.119 (0.8); 8.106 (0.4);
8.097 (0.9); 8.084 (0.4); 8.024 (0.5); 8.022 (0.5); 7.996 (0.4);
7.975 (0.4); 7.352 (3.6); 7.330 (3.5); 7.181 (0.8); 7.159 (0.8);
7.087 (0.4); 7.069 (0.4); 7.067 (0.4); 5.758 (2.8); 4.564 (1.5);
4.442 (3.0); 4.115 (0.7); 4.015 (4.7); 3.988 (16.0); 3.931 (15.4);
3.909 (3.9); 3.568 (0.8); 3.544 (14.4); 3.331 (131.8); 2.676 (0.7);
2.672 (0.9); 2.667 (0.7); 2.525 (2.7); 2.511 (52.5); 2.507 (106.0);
2.503 (139.4); 2.498 (102.4); 2.494 (51.6); 2.334 (0.6); 2.329
(0.9); 2.325 (0.7); 1.259 (0.5); 1.234 (1.5); 0.000 (5.6) I-74 3.36
3.49 Example I-74: .sup.1H-NMR (601.6 MHz, CD3CN): .delta. = 8.905
(3.0); 8.903 (3.0); 8.852 (1.6); 8.850 (1.6); 8.500 (1.9); 8.313
(1.5); 8.311 (2.1); 8.309 (1.4); 8.183 (1.7); 8.181 (1.7); 7.962
(3.4); 7.961 (3.4); 4.001 (16.0); 3.940 (0.4); 3.124 (1.1); 3.111
(3.4); 3.099 (3.5); 3.087 (1.2); 2.639 (0.7); 2.184 (55.7); 2.109
(1.2); 2.005 (2.2); 1.998 (195.7); 1.989 (2.7); 1.985 (1.8); 1.981
(10.0); 1.977 (18.2); 1.973 (26.5); 1.969 (18.0); 1.965 (9.0);
1.882 (1.2); 1.419 (0.4); 1.404 (0.7); 1.373 (0.6); 1.330 (4.1);
1.318 (9.0); 1.309 (1.6); 1.305 (5.2); 1.301 (3.4); 0.914 (0.6)
I-75 2.84 2.94 Example I-75: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
.delta. = 9.582 (2.6); 9.107 (4.5); 8.797 (2.6); 8.794 (2.8); 8.761
(3.5); 8.668 (2.9); 8.361 (4.6); 8.314 (0.3); 5.754 (2.9); 3.939
(1.0); 3.920 (3.5); 3.897 (16.0); 3.883 (1.4); 3.316 (65.0); 2.675
(0.8); 2.671 (1.1); 2.666 (0.9); 2.506 (121.1); 2.502 (165.0);
2.497 (131.6); 2.333 (0.7); 2.328 (1.1); 2.324 (0.9); 1.988 (0.8);
1.272 (3.7); 1.253 (8.2); 1.235 (4.5); 1.175 (0.4); 0.146 (0.5);
0.008 (3.6); 0.000 (102.8); -0.150 (0.5) I-76 3.73 3.84 Example
I-76: .sup.1H-NMR (601.6 MHz, CD3CN): .delta. = 9.334 (1.1); 9.333
(1.2); 9.331 (1.2); 9.329 (1.1); 9.015 (1.4); 9.014 (1.7); 8.867
(2.5); 8.865 (2.3); 8.751 (1.2); 8.750 (1.3); 8.747 (1.3); 8.287
(2.6); 8.286 (2.3); 8.036 (1.9); 5.446 (0.6); 3.879 (0.9); 3.867
(16.0); 3.855 (3.0); 3.842 (0.9); 2.129 (16.5); 1.964 (0.3); 1.955
(0.9); 1.951 (1.2); 1.947 (9.5); 1.943 (17.4); 1.939 (24.5); 1.935
(16.4); 1.931 (8.6); 1.313 (3.1); 1.300 (6.6); 1.288 (3.1); 1.270
(0.6); 0.005 (0.6); 0.000 (19.1); -0.006 (0.7) I-77 3.81 3.90
Example I-77: .sup.1H-NMR (601.6 MHz, CD3CN): .delta. = 9.333
(1.3); 9.332 (1.5); 9.330 (1.5); 8.871 (3.2); 8.869 (3.1); 8.750
(1.6); 8.748 (1.6); 8.736 (1.3); 8.734 (1.4); 8.731 (1.4); 8.730
(1.2); 8.250 (3.0); 8.249 (3.0); 6.869 (1.7); 6.865 (1.7); 5.446
(0.7); 3.884 (1.1); 3.871 (4.7); 3.869 (16.0); 3.859 (3.6); 3.847
(1.1); 2.133 (5.1); 1.956 (0.3); 1.952 (0.4); 1.948 (3.5); 1.944
(6.3); 1.940 (9.0); 1.936 (6.1); 1.932 (3.2); 1.314 (3.5); 1.302
(7.5); 1.290 (3.6); 1.285 (0.4); 1.267 (0.5); 0.000 (5.6)
Use Examples
Ctenocephalides felis--in vitro Contact Test
For the coating of the test tubes, 9 mg of active ingredient are
first dissolved in 1 ml of acetone p.a. and then diluted to the
desired concentration with acetone p.a. 250 .mu.l of the solution
are distributed homogeneously on the inner walls and base of a 25
ml test tube by turning and rocking on an orbital shaker (rocking
rotation at 30 rpm for 2 h). With 900 ppm active ingredient
solution and internal surface 44.7 cm.sup.2, given homogeneous
distribution, an area-based dose of 5 .mu.g/cm.sup.2 is
achieved.
After the solvent has evaporated off, the tubes are populated with
5-10 adult cat fleas (Ctenocephalides felis), sealed with a
perforated plastic lid and incubated in a horizontal position at
room temperature and ambient humidity. After 48 h, efficacy is
determined. To this end, the test tubes are stood upright and the
fleas are knocked to the base of the tube. Fleas which remain
motionless at the base or move in an uncoordinated manner are
considered to be dead or moribund.
A substance shows good efficacy against Ctenocephalides felis if at
least 80% efficacy was achieved in this test at an application rate
of 5 .mu.g/cm.sup.2. 100% efficacy means that all the fleas were
dead or moribund. 0% efficacy means that no fleas were harmed.
In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 5 .mu.g/cm.sup.2: I-18, I-21
Boophilus microplus--Injection Test (BOOPMI Inj)
Solvent: dimethyl sulphoxide
To produce an appropriate active ingredient formulation, 10 mg of
active ingredient are mixed with 0.5 ml of solvent and the
concentrate is diluted with solvent to the desired
concentration.
1 .mu.l of the active ingredient solution is injected into the
abdomen of 5 engorged adult female cattle ticks (Boophilus
microplus). The animals are transferred into dishes and kept in a
climate-controlled room.
Efficacy is assessed after 7 days by laying of fertile eggs. Eggs
which are not visibly fertile are stored in a climate-controlled
cabinet until the larvae hatch after about 42 days. An efficacy of
100% means that none of the ticks has laid any fertile eggs; 0%
means that all the eggs are fertile.
In this test, for example, the following compounds from the
preparation examples show an efficacy of 80% at an application rate
of 20 .mu.g/animal: I-21
Ctenocephalides felis--Oral Test (CTECFE)
Solvent: dimethyl sulphoxide
For the purpose of producing an appropriate active ingredient
formulation, 10 mg of active ingredient are mixed with 0.5 ml of
dimethyl sulphoxide. Dilution with citrated cattle blood gives the
desired concentration.
About 20 unfed adult cat fleas (Ctenocephalides felis) are placed
into a chamber which is closed at the top and bottom with gauze. A
metal cylinder whose bottom end is closed with parafilm is placed
onto the chamber. The cylinder contains the blood/active ingredient
preparation, which can be imbibed by the fleas through the parafilm
membrane.
After 2 days, the kill in % is determined. 100% means that all of
the fleas have been killed; 0% means that none of the fleas have
been killed.
In this test, for example, the following compounds from the
preparation examples show an efficacy of 90% at an application rate
of 100 ppm: I-21
Lucilia cuprina Test (LUCICU)
Solvent: dimethyl sulphoxide
To produce an appropriate active ingredient formulation, 10 mg of
active ingredient are mixed with 0.5 ml of dimethyl sulphoxide, and
the concentrate is diluted with water to the desired
concentration.
About 20 L1 larvae of the Australian sheep blowfly (Lucilia
cuprina) are transferred into a test vessel containing minced
horsemeat and the active ingredient preparation of the desired
concentration.
After 2 days, the kill in % is determined. 100% means that all the
larvae have been killed; 0% means that none of the larvae have been
killed.
In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 100 ppm: I-18, I-21
Musca domestica Test (MUSCDO)
Solvent: dimethyl sulphoxide
To produce an appropriate active ingredient formulation, 10 mg of
active ingredient are mixed with 0.5 ml of dimethyl sulphoxide, and
the concentrate is diluted with water to the desired
concentration.
Vessels containing a sponge treated with sugar solution and the
active ingredient formulation of the desired concentration are
populated with 10 adult houseflies (Musca domestica).
After 2 days, the kill in % is determined. 100% means that all of
the flies have been killed; 0% means that none of the flies have
been killed.
In this test, for example, the following compounds from the
preparation examples show an efficacy of 95% at an application rate
of 20 ppm: I-21
Myzus persicae--Spray Test (MYZUPE)
Solvent: 78 parts by weight of acetone 1.5 parts by weight of
dimethylformamide Emulsifier: alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
Discs of Chinese cabbage leaves (Brassica pekinensis) infested by
all stages of the green peach aphid (Myzus persicae) are sprayed
with an active ingredient formulation of the desired
concentration.
After 6 days, the efficacy in % is determined. 100% means that all
the aphids have been killed; 0% means that none of the aphids have
been killed.
In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 500 g/ha: I-10, I-13, I-18, I-22, I-23, I-24, I-43, I-44,
I-48, I-52
In this test, for example, the following compounds from the
preparation examples show an efficacy of 90% at an application rate
of 500 g/ha: I-4, I-12, I-14, I-17, I-18, I-19, I-21, I-38, I-42,
I-45, I-46, I-49, I-50, I-51, I-56, I-61, I-68
In this test, for example, the following compounds from the
preparation examples show an efficacy of 90% at an application rate
of 20 g/ha: I-39
Phaedon cochleariae--Spray Test (PHAECO)
Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of
dimethylformamide Emulsifier: alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed
with an active ingredient formulation of the desired concentration
and, after drying, populated with larvae of the mustard beetle
(Phaedon cochleariae).
After 7 days, the efficacy in % is determined. 100% means that all
the beetle larvae have been killed; 0% means that no beetle larvae
have been killed.
In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 500 g/ha: I-2, I-3, I-4, I-5, I-10, I-12, I-13, I-14, I-18,
I-19, I-21, I-22, I- 24, I-25, I-26, I-28, I-29, I-31, I-36, I-37,
I-38, I-39, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-49,
I-50, I-51, I-52, I-53, I-54, I-55, I-61, I-68, I-73
In this test, for example, the following compounds from the
preparation examples show an efficacy of 83% at an application rate
of 500 g/ha: I-30, I-63
In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 100 g/ha: I-11
In this test, for example, the following compounds from the
preparation examples show an efficacy of 83% at an application rate
of 100 g/ha: I-17
Spodoptera frugiperda--Spray Test (SPODFR)
Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of
dimethylformamide Emulsifier: alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
Leaf discs of maize (Zea mays) are sprayed with an active
ingredient formulation of the desired concentration and, after
drying, populated with caterpillars of the armyworm (Spodoptera
frugiperda).
After 7 days, the efficacy in % is determined. 100% means that all
the caterpillars have been killed; 0% means that no caterpillars
have been killed.
In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 500 g/ha: I-2, I-21, I-26, I-37, I-39, I-42, I-46, I-47,
I-54, I-61, I-63, I-68
In this test, for example, the following compounds from the
preparation examples show an efficacy of 83% at an application rate
of 500 g/ha: I-14, I-19, I-48
Tetranychus urticae--Spray Test, OP-Resistant (TETRUR)
Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of
dimethylformamide Emulsifier: alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
Discs of bean leaves (Phaseolus vulgaris) infested by all stages of
the greenhouse red spider mite (Tetranychus urticae) are sprayed
with an active ingredient formulation of the desired
concentration.
After 6 days, the efficacy in % is determined. 100% means that all
the spider mites have been killed; 0% means that none of the spider
mites have been killed.
In this test, for example, the following compound from the
preparation examples shows an efficacy of 100% at an application
rate of 500 g/ha: I-68
In this test, for example, the following compounds from the
preparation examples show an efficacy of 90% at an application rate
of 500 g/ha: I-2, I-13, I-19, I-22, I-28, I-42, I-44, I-53
In this test, for example, the following compound from the
preparation examples shows an efficacy of 90% at an application
rate of 100 g/ha: I-48
Myzus persicae--Spray Test (MYZUPE)
Solvent: 7 parts by weight of dimethylformamide Emulsifier:
alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water. If the addition of
ammonium salts or/and penetrants is required, these are each added
in a concentration of 1000 ppm to the formulation solution.
Bell pepper plants (Capsicum annuum) heavily infested by the green
peach aphid (Myzus persicae) are treated by spraying with the
active ingredient formulation in the desired concentration.
After 6 days, the kill in % is determined. 100% means that all the
aphids have been killed; 0% means that no aphids have been
killed.
In this test, for example, the following compound from the
preparation examples shows an efficacy of 97% at an application
rate of 100 ppm: I-11
Meloidogyne incognita Test
Solvent: 125.0 parts by weight of acetone
To produce a suitable active ingredient formulation, 1 part by
weight of active ingredient is mixed with the stated amount of
solvent and the concentrate is diluted with water to the desired
concentration.
Vessels are filled with sand, active ingredient solution, an
egg/larvae suspension of the southern root-knot nematode
(Meloidogyne incognita) and lettuce seeds. The lettuce seeds
germinate and the plants develop. The galls develop on the
roots.
After 14 days, the nematicidal efficacy in % is determined by the
formation of galls. 100% means that no galls were found; 0% means
that the number of galls on the treated plants corresponds to the
untreated control.
In this test, for example, the following compound from the
preparation examples shows an efficacy of 100% at an application
rate of 20 ppm: I-68
Comparative Examples:
Myzus persicae--Contact Test (MYZUPE c)
Solvent: 7 parts by weight of dimethylformamide Emulsifier:
alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water. In the event that
addition of ammonium salts or/and penetrants (rapeseed oil methyl
ester) is required, these are each pipetted in a concentration of
1000 ppm after the finished formulation solution has been
diluted.
One-leaved bell pepper plants (Capsicum annuum) heavily infested by
the green peach aphid (Myzus persicae) are treated by spraying the
underside of the leaf with the active ingredient formulation in the
desired concentration.
After the desired time, the kill in % is determined. 100% means
that all the aphids have been killed and 0% means that none of the
aphids have been killed.
In this test, for example, the following compound from the
preparation examples shows good efficacy compared to the known
compound from WO2013018928 (see table):
Myzus persicae--Translaminar Test (MYZUPE t)
Solvent: 7 parts by weight of dimethylformamide Emulsifier:
alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water. In the event that
addition of ammonium salts or/and penetrants (rapeseed oil methyl
ester) is required, these are each pipetted in in a concentration
of 1000 ppm after the finished formulation solution has been
diluted.
One-leaved bell pepper plants (Capsicum annuum) heavily infested by
the green peach aphid (Myzus persicae) are treated by spraying the
top side of the leaf with the active ingredient formulation in the
desired concentration.
After the desired time, the kill in % is determined. 100% means
that all the aphids have been killed and 0% means that none of the
aphids have been killed.
In this test, for example, the following compound from the
preparation examples shows good efficacy compared to the known
compound from WO2013018928 (see table):
Aphis gossypii--Contact Test (APHIGO c)
Solvent: 7 parts by weight of dimethylformamide Emulsifier:
alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water. In the event that
addition of ammonium salts or/and penetrants (rapeseed oil methyl
ester) is required, these are each pipetted in a concentration of
1000 ppm after the finished formulation solution has been
diluted.
One-leaved cotton plants (Gossypium hirsutum) heavily infested by
the cotton aphid (Aphis gossypii) are treated by spraying the
underside of the leaf with the active ingredient formulation in the
desired concentration.
After the desired time, the kill in % is determined. 100% means
that all the aphids have been killed and 0% means that none of the
aphids have been killed.
In this test, for example, the following compound from the
preparation examples shows good efficacy compared to the known
compound from WO2013018928 (see table):
Aphis gossypii--Translaminar Test (APHIGO t)
Solvent: 7 parts by weight of dimethylformamide Emulsifier:
alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water. In the event that
addition of ammonium salts or/and penetrants (rapeseed oil methyl
ester) is required, these are each pipetted in in a concentration
of 1000 ppm after the finished formulation solution has been
diluted.
One-leaved cotton plants (Gossypium hirsutum) heavily infested by
the cotton aphid (Aphis gossypii) are treated by spraying the top
side of the leaf with the active ingredient formulation in the
desired concentration.
After the desired time, the kill in % is determined. 100% means
that all the aphids have been killed and 0% means that none of the
aphids have been killed.
In this test, for example, the following compound from the
preparation examples shows good efficacy compared to the known
compound from WO2013018928 (see table):
Nephotettix cincticeps Test (NEPHCI)
Solvent: 7 parts by weight of dimethylformamide Emulsifier:
alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water. In the event that
addition of ammonium salts or/and penetrants (rapeseed oil methyl
ester) is required, these are each pipetted in in a concentration
of 1000 ppm after the finished formulation solution has been
diluted.
Rice plants (Oryza sativa, var. Balilla) are treated by spraying
with the active ingredient formulation in the desired concentration
and then populated with larvae of the green rice leafhopper
(Nephotettix cincticeps).
After the desired time, the kill in % is determined. 100% means
that all leafhoppers have been killed; 0% means that none of the
leafhoppers have been killed.
In this test, for example, the following compound from the
preparation examples shows good efficacy compared to the known
compound from WO2013018928 (see table):
Nilaparvata lugens Test (NILALU)
Solvent: 7 parts by weight of dimethylformamide Emulsifier:
alkylaryl polyglycol ether
To produce an appropriate active ingredient formulation, 1 part by
weight of active ingredient is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water. In the event that
addition of ammonium salts or/and penetrants (rapeseed oil methyl
ester) is required, these are each pipetted in in a concentration
of 1000 ppm after the finished formulation solution has been
diluted.
Rice plants (Oryza sativa, var. Balilla) are treated by spraying
with the active ingredient formulation in the desired concentration
and then populated with L3 larvae of the brown planthopper
(Nilaparvata lugens).
After the desired time, the feeding damage in % is determined. 100%
means that no feeding damage is found; 0% means that the feeding
damage to the treated plant corresponds to that of the untreated
control.
In this test, for example, the following compound from the
preparation examples shows good efficacy compared to the known
compound from WO2013018928 (see table):
TABLE-US-00003 Animal Substance Structure species Concentration %
efficacy dat* Ex. I-21 ##STR00060## MYZUPE c MYZUPE t MYZUPE t
APHIGO c APHIGO t NEPHCI NEPHCI NEPHCI NILALU NILALU 2.4 g/ha 12
g/ha 2.4 g/ha 2.4 g/ha 2.4 g/ha 0.16 ppm 0.16 ppm 0.16 ppm 4 ppm 4
ppm 85 98 90 98 65 90 95 100 90 100 14 dat 14 dat 14 dat 7 dat 7
dat 14 dat 21 dat 34 dat 21 dat 28 dat Ex. 5 known from
WO2013018928 ##STR00061## MYZUPE c MYZUPE t MYZUPE t APHIGO c
APHIGO t NEPHCI NEPHCI NEPHCI NILALU NILALU 2.4 g/ha 12 g/ha 2.4
g/ha 2.4 g/ha 2.4 g/ha 0.16 ppm 0.16 ppm 0.16 ppm 4 ppm 4 ppm 50 0
0 15 0 0 0 0 35 20 14 dat 14 dat 14 dat 7 dat 7 dat 14 dat 21 dat
34 dat 21 dat 28 dat *dat = days after treatment (days)
* * * * *